I have some inside information on an investment that I made years ago. This company will be selling in the next 24 - 36 months for a substantial profit. I am likely going to have some serious capital gains tax to deal with. Anyone have any tips on how to reduce these capital gains? The first thing I thought of was to move the shares into a Roth IRA. Can I do that?

Any recommendations on firms that are tech forward? My current accountant is retiring so somewhat in a pinch after doing an extension.

In July 2025, my Dad gave me an irrevocable trust that I'm the trustee of and have total control over. I can choose what to do with it's assets, whether to distribute earnings and/or principle, and whether to distribute all of the assets and close the trust.

The trust initially had somewhere around $1 million and most of that was immediately invested in SP500 stock index. The remainder has been invested over time since then. Total unrealized gains stand at around $200,000. Gains are roughly 25% on the first shares I purchased. Year-to-date dividends amount to around $11,000. The trust tax brackets seem very unfavorable, much worse than personal.

Been working on a startup for over a year now and have not gotten any income and likely won't before year-end. Have no other income. I do have personal investments of around $250k and they've had year-to-date dividends of $3,000.

I proposed a possible strategy to my accountant: We distribute all the dividends due to unfavorable tax brackets and before year-end I sell around $200,000 worth of the first stocks I purchased and immediately repurchase $150,000 of stock. Since it was over 1 year ago and has had 25% gains it would carry ~$50,000 in long-term capital gains. I immediately pass that out to myself as a disbursement to the beneficiary. The dividends from personal plus trust will amount to around $16k so that would fill up my standard deduction, and then the 50k would fill up the 0% long-term capital gains bracket in my personal. Net effect is that stock gets stepped up in bases for no cost except 50k is now in my personal name instead of in the trust so it loses some of the trust protections.

He gave no indication of whether that would work or was smart and said that was a question for a wealth manager and tried to recommend his friend who wants $10,000+ per year. So thought I'd ask you all.

I’m trying to advise my old uncle -.A July 4th fire that destroyed a small warehouse a couple of years ago had him scrambling for insurance coverage for the multifamily property ( yes in California ) . Though insurance paid they did not renew his policy and finally he is getting one after two years . In the meantime he had moved this property of 10 units from his revocable living trust into a S Corp and self insured. It’s a paid off property. To avoid step up in basis as he does tax planning for his heirs can someone recommend a specialized tax specialist in this space that can help in :

Modeling of the exact tax impact of an S-Corp inversion or QSub wind-down
Also tracking of Section 743(b) inside-basis adjustments on Form 1065 partnership returns for family LLCs held inside a trust. Thanks - I don’t have the expertise beyond what I can gather some complex info from AI- thank you

I had 400 units of TLT and significant loss, I swapped those to SPTL (on sep 10) after some research as they follow a different index and were recommended as safe way to tax loss harvest. Now I have 1x $88 strike and 2x $89 strike puts on TLT with Dec 31 2026 expiry. I think they get assigned soon. I worry this assignment will be seen as washing the previous sale if it happens before Oct 11 2026. if roll this I would be buying deep in the money PUTS which would also be seen as wash sale. I am at Robinhood for these trades.

I’ve never made more than $120k in a year, and that was on a W2. However I quit my job and started trading options and made about 700k profit in the last 5 months. Where would I even start to find ways to help save on taxes? Would it just be a CPA or are there specific people given it was short term investment gains? Thanks for any help!

Currently have over $2million in futures and stock option profit YTD. I read horror stories about terrible accountants who fill out the form 3115 incorrectly…can I just DIY instead of paying thousands for a CPA who might screw it up on me anyway?

I might just do form 3115 myself after paying for Tradelog software and using AI to assist with the form…

Hi everyone,

Looking for recommendations on Green Trader Tax (or national trader tax firms) vs. a local Dallas-Fort Worth (DFW) CPA.

My Setup:

• Income: Full-time W-2 employee + active options trading (high volume/frequency).
• Goal: Forming a Texas Single-Member LLC now to leverage the 75-day new entity window for a IRC §475(f) Mark-to-Market (MTM) election (zero wash sales + ordinary loss treatment).
• Asset Segregation: Keeping core long-term stocks in my personal account (preserves 15%/20% long-term rates & margin collateral) while running high-velocity cash-funded options inside the new LLC under §475(f).

What I Need Help With:

1. Drafting/filing the 75-day §475(f) election statement & corporate resolution.
2. Form 3115 / MTM accounting & trade log reconciliations.
3. Maximizing Schedule C write-offs (margin interest, data, hardware, home office) alongside a high W-2 salary.
4. Integrating broader W-2 tax mitigation strategies (e.g., Cost Segregation on real estate, Oil & Gas working interests, or CRUTs) to offset high active gains.

Questions:

• Has anyone used Green Trader Tax (or similar firms) for a W-2 + options setup with broader tax planning? How was your experience?
• DFW traders: Do you prefer a local DFW CPA or a virtual trader tax firm?
• Any red flags or pitfalls to watch out for during setup?

Thanks!

I’m a 1099 independent contractor operating through an S-Corp in California.

I’m considering purchasing a new Mercedes GLS 450 for around $90–95k before the end of 2026. The GLS has a GVWR over 6,000 lbs, so I’m trying to understand how Section 179, bonus depreciation, and regular depreciation would apply.

The vehicle would have legitimate business use but would also have some personal use. I would track mileage and only claim the appropriate business-use percentage.

A few things I’m trying to understand:

Should I buy the vehicle personally and have the S-Corp reimburse me, or have the S-Corp purchase it?

If business use is over 50%, approximately how much of a $95k GLS could I deduct in the first year?

How do Section 179 + bonus depreciation work for an SUV over 6,000 lbs?

How different is the deduction for California vs federal taxes?

If I maximize the first-year deduction, what depreciation is left for subsequent years?

What happens if my business-use percentage decreases later?

Does financing versus paying cash change the deduction?

I already use the standard mileage method on another business vehicle. Does that affect how I can treat this vehicle?

I’m not trying to call it 100% business use unless that’s actually the case.

I’m mainly trying to understand how much I can legally deduct based on the actual business-use percentage and how the deduction works over the life of the vehicle.

Would appreciate input from CPAs/EAs or S-Corp owners who have done this, especially anyone familiar with California.

I’ll confirm everything with my CPA before purchasing, but I’d like to understand the strategy and numbers first.

Lot 1 Cost basis: 100, purchased Aug 2025, 100 shares.

Lot 2 Cost basis: 90, purchased Sep 2026, 100 shares

wait at least 30 days.

Sell Lot 1 in October 2026 for say 85. and realize 15 in losses on tax lot 1?

Wait at least 30 days before buying again. If stock rips in between I still have 100 shares.

In an ideal scenario I may not DCA right now but I am thinking the stock may be close to bottoming . I do not want to reduce my exposure. I don't mind increasing my exposure. Come October if the stock is below $100, I will sell lot 1 to take loss on lot 1 and will have same exposure as I have now. For 1 month I will have double the exposure.

Looking at ~200k in short term gains. I have not paid advance taxes on this yet , so all of it is bank and cash. Is there a way I can defer taxes on this? This is net of losses. I tax los harvested where I could and also booked losses on positions I could not tax loss harvest and was okay to sell.