Short Answer is yes, via interest tracing rules. 

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

The Short Term ShowThe Short Term Rental Management ShowThe Short Term Shop all day long.

Short-term rentals are becoming oversaturated in certain markets plus anti-STR legislation is resulting in some of those properties also converting to long-term rentals.You already have the operations experience by self-managing.

Which reminds me that I should mention that I’m not opposed to living a not-so-luxurious lifestyle in the short run.

. - some strategies I've seen California investors use to lessen negative cash flow: house hacking, mid-term rentals (people temporarily displaced from home renovation or insurance reasons like fire), rent by the room, Short Term Rentals. - The ultimate house hack, live in the small ADU unit and rent out the two levels of the main house on AirBnb in San Francisco (I would have thought STRs are oversaturated in S.F. but it worked for them and they stay fully booked).

Short Term: No, not happening. 

Not to mention short sighted as you are now finding out.

Welcome to BP and come on over to the Short Term Rental part of the forums.  

I'm trying to analyze my first property and not sure how to set it up to run the number using the calculator tools here. 2 of the units are successful Airbnb short term rentals, and the other two units are month to month rentals to existing tenants.