The mortgage guy told me the other house would be treated as an ADU and give me no real value towards the value of my future mortgage.Not sure if that helps much?

At present, I do not have full access to MLS data, though I do intend to obtain my real estate license in the near future.

Currently speaking with a local realtor about the STR zoning issues, insurance issues, and current/future market in Florida. 2025 should be a good time to look for a property there. 1.

This is something I will have to keep in mind for myself in the future.

I would NOT remove any money from index funds as I expect those to be a great earner into the future and very steady hedge against other avenues.

Is their current portfolio distressed, or was the majority of their current portfolio purchased at the peak of the market, indicating that they might be in distress in the near future. 

Land that you're not personally developing most of the time falls into two categories - either you're speculating that development is coming that way, and will increase the demand for the land, or you're changing the current permissible use of the land in such a way that it will be worth more money now or in the future.

I would prefer to pay the capital gains today as based on how we spend money as a country, that capital gains rate most likely is going to be heading up in the future not down.

If you value simplicity and future flexibility, consider selling and reallocating through a 1031.

Look forward to having you walkthrough in the future