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.

This plays into the affordability issues for tenants by allowing them to live in nicer neighborhoods for less money, yet I get monthly revenue comparable to short-term rentals.I have also shifted my focus to buying better.

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

Here's what works for me: 1) Posting your property on Facebook Marketplace2) Craigslist3) Talk to local universities or big corporations who may need short or long term housing for their clients4) Property managers are hit or miss.

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

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.

. - 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. 

With one property you can self manage even from a distance.