If I were choosing strictly between NY & FL, I would definitely choose Florida- NY has more taxes & restrictions.

If there COVID impacted it will not be possible to get them out until the year ends with the CDC eviction restrictions.  

If there is no Hoa and builder is no longer there, it was done in 1993.Who would confirm if there are covenants and restrictions?

Thus the bulk of the restriction would be on new owners.

There is a proposed residential tenant-landlord ordinance in Cook County, which would put more restrictions on the way you conduct your rental business.

STR restrictions?

If there are no major restrictions, you will also need to work with the city development department to ensure you are providing the proper parking, fire protection, etc.

We have gone with a portfolio lender because of less restrictions on the debt-to-income ratio. 

Once they know that you're for sale, there's at least some chance they'll tighten your credit lines or even put you on COD - and that's probably going to come up during your buyer's due diligence.And when will your buyer think when he discovers unfavorable credit terms with your key vendors? 

Your attorney will be better able to address the specifics, but I've always been advised to form the LLC in the state I was investing in, though I don't think there's any restrictions to investing in MA with a NY LLC.