How can I save my house from the chopping block?

Please see an attorney now.
You cannot mess with this without help.
It is sounding to me, with your mom, as you saying being the only name on the deed that she did NOT move these properties into the trust.
The TRUST should now be the owners of these properties, not your mother. Otherwise the trust cannot administer these properties and what the trust says about them is entirely irrelevant.

People who often make Trusts don't understand them at all.
They fail to legally file to get their deeds/properties filed as now belonging to a Trust.
If they don't do this the Trust is worthless. And the properties still simply belong to "mom".
If she is the owner of TWO properties I don't even see how she GOT medicaid, let alone understand what clawback would be.

You need an attorney right away.

I was under the impression Trusts are formed to protect assets from Medicaid. If done over 5 yrs when Medicaid is needed, the condo and house are not considered part of Moms assets. There is revocable and irrevocable. You need to find out want these trusts are.

You do need to see the lawyer that wrote the trusts. If irrevocable youbhave no problem. Trusts are done to protect assets and to bypass probate.

When we created our trust, it protects our home from probate and Medicaid, but the same may not be true in your state or your Mom's trust. Also, we own our home, no mortgage. Trusts are complicated and you should not be asking an anonymous global forum of non-professionals for advice. Please seek counsel from a CPA, tax attorney, estate planner, financial planner, NYS Medicaid Planner and/or a Bank & Trust organization. Sounds like your SIL is the Trustee. In the future I would not take advice from him without having it vetted by a professional.

The 5-yr lookback rule won't apply once a transaction is outside that window of time without your Mom needing to apply for Medicaid. But no one can predict this. I'm waiting for 2024 to end since it will be the 5th year post-purchase of my Mom's house (she's currently 94 and her cognition is nose-diving but she still has a reasonable amount of funds left for her care).

"I had to take money out of her investment account to cover the gap between LTC and reality and my son in law, who managed the account for her, never advised me against doing this and the tax implications I'd face."

You faced? Not your Mom? Was it your money? Seems like it was your Mom's... so not sure why you'd have had tax exposure on this action.

If you do purchase her house, for purposes of Medicaid scrutiny it must be at FMV. But do get professional advice before doing anything. It may seem expensive to do this but as you've found out it will be more expensive at tax time if you don't.

I agree that you need to consult an attorney with expertise in Medicaid in the appropriate state.

If the LTC insurance, the investments, and the condo proceeds will cover care for 5 years, then it may still be practical to transfer the title to you, assuming there is a POA with authority to do this. Bring any paperwork that you have to the meeting with the lawyer. The LTCI paperwork should indicate if it is a “partnership” policy that allows more assets to be kept while qualifying for Medicaid.

A tax preparer can look at her income, including any capital gains, and see how much the unreimbursed medical expenses for her care can be deducted. If 2023 only included only a few months of care, there may be some taxes due, but it probably isn’t as bad as you fear.

I doubt your SIL can be held liable; I wouldn’t recommend pursuing it if he has been pitching in to help as an unpaid family member, but if he’s been well paid for his services, I’d be tempted to replace him with a fee only distribution planner who does tax planning.

You’d probably like a projection of what each of the next five years taxes could be expected to look like. An explanation of “step up in basis” on inherited assets should also be sought so you’ll have a better idea of balancing the risk of dying too soon against the risk of living too long.

If mom has a LTC policy and two houses, it's highly unlikely she'd need Medicaid in the near future, especially if your sister is willing to have the condo sold. Of course how much is realized from the condo sale depends on how much is still owed on the mortgage. Presumably mom also has social security and perhaps possibly a pension? Those should also be going for her care. You mention having to take money out of Mom's investment account to help cover what the LTC insurance doesn't cover. Are you mom's POA? If not, hopefully you have proof or documentation that she authorized this (unlikely, since you say she has dementia). In any case, her money was used for her benefit, so I don't see how there could be any problem with this. As to tax implications, if there were capital gains on the sale of investments, then your mom would owe taxes on that--you yourself wouldn't face any tax implications. If there was a loss on the sale, then up to $3,000 of the loss can be deducted from her income when filing her taxes (if loss is greater than that, it carries forward to the next year). The brokerage statements (1099B) would give that information.

Trusts are beyond me, so I have no idea what the Medicaid look-back implications are of the bank having you assume the mortgage. I don't think Medicaid cares who's paying the mortgage, except that if mom is applying for Medicaid all her income would need to go toward her care so she wouldn't be able to pay for a mortgage or any other house expenses. More important than who is paying the mortgage is whose name is on the deed. Even if you assume the mortgage, if your mother's name is on the deed Medicaid would consider that she still owns the house, as indeed she does legally, and they could put a lien on it.

This is not the place to get the best advice. Invest in an elder care lawyer with Medicaid experience.