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. 

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.

Thanks Yes I have done age restricted communities  They are no different than any other subdivision than the density granted due to the age restriction.

Also, often there are rental restrictions like no rental use for 1 or 2 years.