I think the problem is this...Legislation and government is making it too difficult to be a landlord.

There is legislation pending that would allow it to be done without a City Council Ordinance, but it's unclear if this legislation will pass. 

The other potential problem is the term of the proposed renter not sure exactly we are going to deal with their lease when it comes time to sell.  

The Democratic bill proposed seems to offer funding to landlords while the Republican bills offers landlords nothing. 

Quote from @Riaan Knoetze: @Mike Lambert @Rui Dias Costa,Can you maybe share a high-level list of the proposed AL changes?

Federal ProtectionsFederal protections against predatory lending begin with a veritable alphabet soup of legislation, including TILA, HOEPA and RESPA.13. https://www.lexology.com/library/detail.aspx?

Once you have selected this market, begin doing researching on the current regulations as well as the political climate regarding STRs in that market and whether or not there are any upcoming proposals on the market docket that may shift or change the current regulations.

Propose starting small, like a single-family rental or house hack, with a clear, low-risk plan to minimize concerns.Leverage your industry connections and offer to handle the initial responsibilities, demonstrating your commitment and capability.

It is very much case-by-case and requires understanding of the current regime for personal itemized deductions, as well as gambling on the proposed changes to this regime by the current administration.

100% leverage, which is what it sounds like you're proposing, is high risk.true private money IMO is someone already in your network - your uncle, your dentist.