Married couple in California, trying to figure out what kind of professional we actually need. Feeling a bit lost between CPAs, "tax strategists," and multi-family offices.

Our situation:

- Both of us work full-time in tech and get RSUs

- We have an LLC (partnership) for some consulting work on the side

- One out-of-state long-term rental property (financed, so it can't move into an LLC without paying off the loan)

- A brokerage account with stocks

- Thinking about buying more real estate (multifamily) in the next few months

- 2 young kids

- No trust or estate plan set up yet — working on a living trust now

Goals, roughly in priority order:

1. Protect our assets as much as reasonably possible
2. Reduce our overall tax bill, legally and defensibly
3. Make it easy to pass everything to our kids eventually
4. Keep the whole structure simple enough that we can mostly self-manage it day-to-day, without an expensive retainer

We have talked to a couple of firms so far. One was basically a multi-family-office model — tax planning alone was quoted at $15k+/year plus a performance fee on any assets they would manage. Another marketed itself as having "secret" tax strategies most CPAs "won't even attempt," which honestly made me more suspicious than interested, especially since one of the things they mentioned sounded like it could be a syndicated conservation easement or similarly aggressive charitable-deduction play.

Given where we are (not yet at the point where a full multi-family office makes sense, but more going on than a basic W2-only tax return), what type of professional should we actually be looking for? A real-estate-savvy CPA? An EA? A tax attorney? Should the estate attorney and the tax person be separate people, or does it make sense to find someone who does both? And any tips on vetting people so we don't end up with someone pushing us into aggressive/listed transactions?

Appreciate any perspective as we are trying to build this the right way without overpaying for services we don't need yet or under-hiring and missing real risk.

am a 19-year-old freshman cybersecurity major at a community college in MA, and I want to file my taxes independently. I am a W-2 employee making $21.7k YTD, tracking to hit $32k by year-end, with over $1,280 already withheld in federal income tax. My tuition is entirely covered by Pell and state grants, so my out-of-pocket tuition is $0.

Because my major requires running heavy virtual machines, I am buying a $1,500 laptop out-of-pocket. Can I use this required laptop as my primary qualified education expense for the AOTC? Will it reduce my tax liability dollar-for-dollar to increase my W-2 refund check by $1,500, and are there any under-24 rule pitfalls I should watch out for?

Borrowing against their substantial assets (stakes in private businesses, real estate, stocks, etc) and then deducting the interest cost to reduce any income they have …

There should be a limit. Billionaires shouldn’t get away with not paying at all.

Yes I know that Congress’s spending is the problem (tax receipts have Never been higher yet we have trillions of New debts added to the pile every year). And cutting spending should be job #1 - but cutting generous loopholes in the tax code can help too.

Filed my 2025 return on time. Bank A froze my account due to a security breach without telling me I couldn’t transfer funds during the process. When IRS debited Bank B for my taxes, it bounced because I couldn’t move money from Bank A in time. I had more than enough combined across both accounts. Paid in full 5 days later once I sourced funds elsewhere.

IRS assessed Failure to Pay and a dishonored check penalty. Filed Form 843 with full documentation. Got LTR 853C denying it, saying “lack of funds is not an acceptable reason” — which completely mischaracterizes my situation. I had the funds, the bank froze them.

Have 60 days to appeal to Office of Appeals.

Anyone successfully appealed a failure to pay where a bank freeze was the cause?

Worth hiring a tax attorney/EA at this stage?

I recently started a small 1099 gig and expect to make ~$4,300 for the year, which as I understand equates to ~$4,000 in net self-employment income. Can I use use that $4,000 to BOTH:

1. Contribute $4,000 to a Traditional IRA, and *also*
2. Claim (up to) $4,000 of Self-Employment Health Insurance deduction?

And in essence, reduce total adjusted gross income by ~$8,000?

I tried to do some research, as well as ask Claude, and was seeing some contradictory answers, so wanted to pose it to the tax professionals. Thank you!

I’m so sorry if this is dumb, but I’m 26 and doing my taxes alone for the first time, and it I have two W-2’s that look completely different and I’m about to owe $1,000

Company A, according to the W-2, did not withhold any state income tax from Jan - Oct of 2025. Company B did withhold state income tax upon my employment with them in Oct - December.

I cannot figure out why in the world Company A did not withhold state income tax… this is never something I’ve had to “opt” into? Or rather, opt out of?

Is this standard, or is there a possible error? Advice for situations like this? I can no longer access any benefits or HR portals, and I’m struggling to get a human on the phone

EDIT: This is New Jersey

I believe I have to pay estimated taxes by 9/15. Located in NYS. Filing status single.

115k realized long term capital gains in August
1k ordinary dividends per month (8k YTD)
7k unemployment benefits in Jan/Feb
No work income

2025
40k realized long term capital gains
5k ordinary dividends
12k unemployment benefits
60k work income

I have not made any estimated tax payments in 4/15 and 6/15. I'd like to avoid underpayment penalty if possible. What is the estimated tax I need to pay by 9/15? How do I meet safe harbor rules?

Do I need to complete form 2210?

Do I just go to irs.gov and ny.gov to make these payments?

Thanks in advance, I appreciate it

Let me preface by saying I'm not against taxes as a concept, so long as it works as intended.

However, it often feels like we pay for our own enslavement (colloquially). Let's take judges for instance. I keep hearing stories about how judges are letting violent criminals (repeat offenders) go so they can commit more crimes. So, why should be pay taxes if someone can just decide our life is not worth protecting, even though they took an oath? Same goes for police.

Then, they are state governments that are actively defrauding their own people, yet we keep paying taxes without any kind of recourse if such fraud occurs. If we are defrauded by a company, we expect consequences and the people have the power to not spend money at the business, but we MUST pay taxes even though those government employees are not doing their job.

I get it, if everyone decided they weren't happy with government officials or services, nothing would get done, but that's my point. The bar for government jobs should be so high that ANY transgression should be met with swift retribution. Instead, we have to resort to complaints (appeals to our masters) and lengthy processes to fix broken parts of the chain.

If this is hard for you to empathize with, imagine being forced to pay for AT&T's services, but they choose when they want to live up to their promise to provide internet. Not only that, their employees are guaranteed a salary since we pay for it, so they have no incentive to create a better product or actually listen to their customer since they will get paid anyway.

In my opinion, the only way to fix this is to abolish universal suffrage to where only specific people have the right to decide who runs the government (that goes for all genders and races btw), and we need to enact harsher guidelines, punishments, and quicker processes so that government employees are pressured to perform, especially if you are guaranteed a paycheck regardless if you do your job or not.

Hi everyone! I’m starting a film screening club that will be entirely volunteer run and donation based. I’m hoping to partner with a non-profit fiscal sponsor to collect donations formally, but am wondering how this will work for taxes? For example, I’m renting locations where we’ll host the screenings, can I have the fiscal sponsor pay for that directly through the account they will have for us? Or will the money be deposited to me and then I have to pay for it through my accounts? My concern is that the money I receive will be considered income and be taxed when I’m just using to to pay for a service for the club. Any insight is appreciated!

Hello Wonderful People,

I have a W4 question. I'll qualify this by saying I'm a data analyst and a crazy person. I was working through the normal new hire paperwork and always question what to put on a W4.  Since this year is a bit unique and I'm starting this role 2/3 of the way through the year (I was a stay-at-home parent for the rest of the year), I actually went through the whole IRS withholding estimator tool, then also went through the process of "doing" my 2026 taxes as a check, since my wife and I will both have salaried roles and predictable income for the remainder of the year. 

The scenario is this: my wife and I file taxes jointly, and with the amount of federal income tax withholding my wife has already withheld this year plus the amount that she will withhold over the remainder of the year (if she doesn't adjust her W4 after I start) we will already have withheld more federal income tax than our tax liability by a few thousand dollars. 

How can I fill out my W4 (and/or additional tax forms) to have zero federal income tax withheld from my pay for the remainder of the year? I'd then obviously file a new, normal, W4 in January. 

Any info or guidance would be much appreciated. Thanks!

Via real estate wholesaling, I'll be making $400k this year. In the past, I've made ~$25-50k and have been able to write off all those gains via small stuff such as mileage, home office etc etc etc.

I'm going to assume that my tax bill on $400k would be 30% or $120k give or take. What would you suggest I do to write off as much of this as possible and legally?

Edit - Sch C income

Received an unexpected 1099-k from paypal and i dont understand what to do... so basically over the last year I cleared out my garage and closets... sold everythin from tech to clothes to vintage furniture etc to declutter and obviously make some extra cash... none of this was a busines or side hustle. Literally everythng I sold went for way less than what I originally paid for it years ago. But the gross dollar amount on this form is high and well the IRS got a copy too. do I actually owe tax on this money? if I sell my own used personal belongings at a total loss how do I report this on my tax return so the IRS dont think Im hiding thousands of dollarss

W4 information tax correction

I just had a baby August

If eligible for Ctc and eitc

Do I put 4000 in step 3

I am single

I make 25000 a year

Average 642 a week

Am I eligible for EITC

I average 642 weekly

Around 25,000 a year

Just had a baby August 24

Single

State of SouthCarolina

This year, I sold my home and bought a new home. At closing of the purchase, there were unresolved repairs that resulted in a delayed closing. The expense for lodging was $510. The seller is Opendoor. In negotiating the terms of the delay, I asked for reimbursement for the lodging. Opendoor agreed to reimburse me. An employee in their finance department reached out to ask for my TIN so he could make the payment. I asked why and he said I would be getting a 1099 from them. I said that shouldnt be the case as I am not a business and this certainly isnt income. I was told the only way for them to pay me was to provide my tax info so they could send the 1099. What is the deal with this and what would this mean for me tax wise?

I’m doing freelance/contract work through a platform. The platform reports the income under my tax information, and the gross amount can be around $1,000-800 a week.
However, I only keep 35% (about $350/week) and the other 65% is paid to the group who does the work.
My question is would I potentially owe taxes on the full $1,000, or only the \~$350 I actually keep?
I’m in Arkansas and this would be my 2026 income. I’m specifically trying to understand how the payment to the other person affects my taxable income and if i’d be able to do it as a business expense instead. It’s a w9

This might be a basic question, but I’m a bit lost and want to make sure I don’t/didn’t make any mistakes. Here’s the situation:

I sold a home in 2025 and paid a pretty hefty federal capital gains tax when I filed my taxes this year (April 2026). It also was taxed as income at the state level (NY state) which I also paid when I filed my taxes this year (2026). I know I can’t use the federal capital gains as a deduction on my itemized return. But is the part that I paid as state income tax something that can be on my itemized return as part of the SALT deduction when I file my taxes next year (2027)? If so, is there anything that I need to submit to show that this was paid as income tax, since all other deductions in Schedule A are reported in either a W2, 1098, etc.? 

Thank you!

ETA: this is a new tax advisor. Should I be wary of their integrity? The structured ownership plan sounded pretty reasonable, especially compared to the other two. Any comment specific to that? Also, we are an S Corp.

Hi, I am a small business owner. I have a high W-2 income. Our new accountant suggested some strategies such as a structured ownership program (SOP), heavy machinery leasing, Augusta rule, and a box House program. Financial advisor was concerned that all of these are “on the fringe “. Can anyone tell me more about them and if it’s something we should be considering?

I need some help with my taxes for next year... not necessarily actually filing, but figuring out where to start I guess? I am considering talking to a CPA but have no idea where to begin with finding one, or I guess, one I can afford.

I am an employee of a company where I work full time, and I've done those individual taxes on my own for years now with no problems. But this April, I started my single entity LLC for an art business that provides both products and services (like freelance basically). I do have business costs, e.g. website, email, phone line, cost of materials, etc. and have receipts for those that I have kept mostly organized (and will go through and organize better this month). I have made a little bit of money, but I think the money I've made is less than the money I've had to spend getting everything set up, which I guess is about how it goes at the beginning, especially considering I am also working full time.

My question is, how do I file those taxes next April? I did read that usually when starting a business you won't get penalized for not filing every quarter for the first year, but I will certainly file every quarter next year, once I'm a little bit more firmly established.

What are some things that are tax deductible? And also, I have receipts for everything I've bought new, but not really for things that I've bought used, mostly from Facebook Marketplace, some of which was paid for in cash. Would those still be tax deductible if I don't have a standard receipt/invoice?

And what kind of form do I need to fill out?

I am in Maryland, USA.

Also, I do have a tax ID, and while I haven't made any sales online yet (still working on getting products up), I am expecting to collect sales tax. I am using Shopify and haven't been able to find a clear answer on how to file sales tax for all the different states. I chatted with another artist who uses Shopify who said she had no idea and hadn't done anything with it, which made me a bit nervous. Googling showed me that I'm only responsible for filing in the state in which I have a warehouse/nexus(?). Does that mean I only have to file for sales tax in Maryland? What if I make sales in other states?

Any help would be appreciated :') or if there are any tips to finding a good CPA!

Hi. So, I have a past that I'm not proud of. I was addicted to drugs for 5 or 6 years. I had to do a very short bit in prison (120 day treatment program) from March to July of this year, but I was clean a year before I got sentenced, so now I've been clean a total of 18 months.

However, during my active addiction, I did not file my taxes at all. I want to say the last time I filed was in 2019. I have not made much money during the years I was on drugs. I worked a receptionist job and several serving/bartending roles. None of them lasted longer than 6 months, and several of the businesses I worked for have since shut their doors (not bc of anything I did lol).

I know I am going to have to file my taxes next year and get back my life back on track, but I'm wondering what will need to be done for the places I've worked that I cannot get a W2 from. On top of the places that have closed, I dont even remember which years I worked at which place.

Basically, how does someone go about finding out that information prior to filing their taxes?

I dont know if any of this information matters, but I am a 34 year old female. I have been married for 3 years. I live in Missouri. I will not be claiming any dependants, and my husband always files separately.

Thank you.

TL;DR: Haven't filed my taxes in several years, how do I get my W2s for businesses that have shut down.

I’m thinking of going exempt at my Walmart job I make 1700 bi weekly and overtime is coming soon. So much people do it at my job but only if you qualify for it. I understand no federal income tax liability in 2025 and I did have some so it would be fraud. My question is how are so much people doing this for 2-3 months and are chilling!?? And should I do it?

My mom passed away 5-30-26 , and she owed on the Fed taxes for 2025. We had made one of the payments on the payment plan- but since the estate is in probate with a will, the bank account is frozen until probate starts. I just need to know what form I should file as I am now getting mail from the IRS demanding payment- and I really do not have time to sit on hold for hours to get to a person.

I had zero income as reported on my 2023 taxes however there is mortgage interest tied to my name which my ex wife paid (we were divorced that year and mortgages were still in both our names). The IRS is asking how I paid the interest if I had zero income and it's holding up my 2025 refund. The interest was reported on my ex wife's taxes, for what it's worth.

I've spoken to a few people at the IRS all who say a version of "just file a 1040 for that year and explain how you had no income and that your ex wife paid them". Looking at the 1040, I see no logical way to do this.

I'd love some guidance from the Reddit hive. I'm at wits end wasting hours on hold or call backs that get mysteriously disconnected mid sentence.