other posters have started threads saying they're going to buy STRs for tax savings... and this doesn't make sense to me.  

Rent payments from the medical LLC are fully deductible as a business expense, while the property-owning LLC will report the rent as taxable income, which can be offset by deductions for expenses like mortgage interest, property taxes, maintenance, and depreciation.To ensure compliance, document how FMV was determined—using market comparisons, an appraisal, or similar data—and draft a formal lease agreement outlining the terms, rent amount, and responsibilities.

The property tax savings are going to be in the ball park of 40-60%, but to be safe you should double your expected repairs budget when calculating the NOI.If you have any other questions, or want a more in-depth response, I would love to help!

I’d love to hear your thoughts, tips, or even warnings.

Technically it would be best to get a C Corporate or S Corp. to flip properties and since you are considered a dealer if you do several properties a year and this could have negative tax consequences in an LLC.

I would search the BP forums because your tax / legal related questions likely have already been asked.However, it doesn't hurt to still ask the forum what your questions are.

Since the trust is a disregarded entity, the benefit is bypassing  probate, not tax issues or liability concerns. 

However, these programs typically qualifies borrowers based on their income, such as tax returns.The DSCR would be a good option considering you and your husband are entrepreneurs and the tax returns don't look good on paper.

The fact that you have a TAX-FREE income is crazy good.  

I've worked with some Canadians buying  here in Ohio.Indeed, rather than selling your stocks to fund investments (and lose out on any potential price appreciation and dividend payments, as well as incurring capital gains taxes), a nice alternative is to borrow against some percentage of the holdings.You would start with the brokerage where you hold the stocks and see what their loan program looks like for the account you hold.