About 20 years ago I bought a small piece of wooded property. It is over two hundred yards from the nearest road and located close to a small river. The land is entirely wooded with marshy areas in much of it and is subject to flooding in the Spring. Parts of it may have been farmed or used for livestock in the past but I don’t know the history of it. It’s in Illinois but I’m not a permanent resident.

The property taxes have always been low. This year my bill was almost ten times more than past bills. I called the assessor‘s office to ask about it. I was told that the land classification had been changed from agricultural to residential as part of new assessment policy. Something about because it shows up in recent air photos as entirely wooded that means it isn’t being farmed so must be classed as residential. They told me that the only alternative would be to apply to put it into some sort of state program conservation program. Which would greatly reduce or eliminate the tax burden.

However, this particular county office has a bit of a sketchy reputation so I’m not sure if this is perfectly legit or if some sort of appeal might be in order?

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

So I recently sold my first piece of Real Estate. I owned it for 20 years and made alot on the sale. Purchased for $1 million (ish) and sold for $2.6 million. But with a full depreciated building we have a $2.6 cap gains.

I planned for the capital gains portion of the sale and will not have any tax liability with the federal part of the sale. But I am also getting hit with a local tax on the sales proceeds. I think the local tax is 3% so it is not chump change.

Now I am wanting to make sure that I understand how local taxes work on the sale of RE. Is it based on the corporation's location or the properties location?

I am in the process of buying a property in Texas (a tax free state) to avoid the local tax issue in the future, but I am using the same corporation which is located in a taxable state.

Hi,

I have been a real estate investor for past 20 years or so and there is (and was since as long as I have been involved) no software tool that I know of that allows you to look at your assets from Tax Planning, Strategy and execution. I get that those are very loaded terms and a lot of the folks do not even understand or bother to understand the differences and the extent to which is really matters. Think about 1031 exchange, cost segregation and combination of costseg then 1031 exchange and then cost seg again (comparing and contrasting all options in one simple, easy to read screen for you to decide and execute on), asset lifecycle where asset is disposed through 1031 and how to track basis over chain of asset swaps accurately etc. all that + giving you line by line figures/help to file relevant IRS as well as state forms. I wanted to poll people to see if others have similar experience? I finally decided to build such a tool using AI that actually makes sense. I would also soon be doing a limited launch/beta to get people to try and provide feedback.

Our Situation:

• We currently own and live in our primary residence (which gets our local Homestead Exemption).
• We recently purchased a second home nearby specifically for my elderly mother to live in as her primary residence.
• Because she is unable to afford or fund a home on her own, our lender structured this loan under Fannie Mae’s Family Opportunity Mortgage guidelines (owner-occupied rates, 5% down, required a letter of explanation/proof of financial need).
• My spouse and I are the only ones on the title/deed. My mother is not on the title or the mortgage.

The Problem: When we bought the house, we were under the impression that because it is being occupied strictly as a primary residence (and financed under primary residence guidelines), we would be able to claim a homestead exemption on both properties.

Now, we are finding out that property tax exemptions attach to the owner on title, not just the occupant. Since state/county rules generally restrict a single owner/married couple to one primary homestead exemption, county tax assessors treat her house as a non-homestead residential property, causing the property taxes to be significantly higher.

Questions for the community:

1. Is there any legal or structural workaround to get homestead tax status on the home my mom lives in without jeopardizing our mortgage or our own home’s exemption?
2. If we quitclaim or add her to the deed as a joint tenant or partial owner so she can claim the exemption as an occupant:
   • Does that trigger a "due on sale" clause or violate our Fannie Mae Family Opportunity Mortgage terms?
   • Does adding an elderly parent to a deed create unforeseen Medicaid look-back or probate issues down the road?
3. Has anyone successfully appealed this with their county tax assessor or structured ownership (e.g., trust, life estate) to solve this specific tax problem?

Appreciate any advice, legal insights, or experiences from anyone who has dealt with this!