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

Short Answer is yes, via interest tracing rules. 

I’ve been hearing some chatter about large hotel chains lobbying significant funds to push for regulations or outright bans on short-term rentals like Airbnb.

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.

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

--------------------------------------Context:-My wife and I file taxes jointly and own 4 long term rentals in NJ and 3 rentals in FL (1 long term, 2 short/medium term).

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.

Even if I have a claim every 10 years I will have saved $80k over that time period compared to the people who pay for better insurance.

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.

. - 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).