Mind Excess Business Loss Rules.

There are plenty of ways around an HOA but they tend to break the rules that you committed to following.

By the way, 3 of the 4 have been rented since I owned the property so yes I suppose the 75% rule could apply then.

There are neighborhoods across the US where you can take these vintage properties, undertake complete renovations with all new mechanicals, roof etc. and come away with a properties  that costs far less than building the identical building with todays costs.  

Second, I'm a rule follower when it comes to permits.

The general rule around here is 2bedrooms and less will do well on Furnished Finder + airbnb/others.

@Raj VardhanI agree with @Evan Polaski regarding the 6-Month Seasoning Rule: Most traditional lenders require a 6-month holding period before you can do a cash-out refinance.

Oh, forgot to mention, this was prior to self rent rules. 

Not every state or city mandates that any landlord has to accept Section 8, because the landlord has to not only subject their property to Section 8 inspections, rules and regulations, they also often have to separately arrange for the tenant to pay the non-covered part of the rent and can face difficulty evicting just based on that.

@Robby Sanchez rules of thumb don't work, as others here have stated.