@Kettly Soivilien the biggest thing would be finding out what rules and regulations the HOA has in regards to short/long term rentals.

I would recommend narrowing based on location, price, and rental market potential, then by restrictions/ordinances.For example, Indian River Shores (beachside in Vero Beach) requires that residents who rent out their homes through websites such as Airbnb and HomeAway to have a town license; meet fire and safety codes; pass a building inspection; and conform to town regulations for parking and noise. 

The building's by-laws do not have any regulations about smoking.  

Wholesaling sits "outside" of the regulated arena, sort of. 

Because there's a thin line between you and Paine Inc. and a lot of opportunity for mischief, the IRS scrutinizes this structure very closely and has strict regulations on how they are ran.

I've read posts on BP about this sort of thing becoming a syndication, a fund, etc. which is all regulated by the SEC. 

Even regulators in the bank sector treat multifamily differently than other CRE assets, and that is because it has an inherent risk aversion to a market cycle.”While class-A apartments will certainly see some dip during a recession, workforce housing should remain stable if not better performing as demand for attainably priced units increases.

You should review the ADA and any local laws and regulations you have about accessibility.

And then there's HOA and city regulations etc.

Not sure If there are really any regulations for this or not.