Hello,I have had a short term rental that is not compliant with my HOA. 

Update: It looks like the county has appointed an 11 person short term rental committee to review the work, investigate more, and provide a recommendation and will be disbanded by November 30th. 

My wife briefly help a friend manage their monthly short term rental in San Francisco while they were traveling and have a few friends that do it.Monthly rentals seem to book pretty well, but not at a significant premium to long term term rentals. 

I'll keep this short and simple.

@Jon Martin  I agree and in short term its just not worth what you will get in reviews for something like this. 

It seems to me though your short term objective is to get the HOA to take immediate action on the roof.

Hey @Marc Shin, so yes on the games.

There are multiple ways to invest in RE: single family, multi-family,  long term rentals, mid-term rentals, short-term rentals, rent by the room, commercial, co-ownership, syndications (I personally won't do syndications) etc. 

If appreciation is not there, however, it seems like a potentially long waiting game to see if your $60k investment today returns anything meaningful in the long run. 

Short Answer is yes, via interest tracing rules.