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

Brokers either get leads through a network of brokers in other disciplines or organic contacts.

You can lead a horse to water but you can't make the horse learn math.

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. 

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

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

But the short answer is this:   You're on the right path. 

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. 

Short Answer is yes, via interest tracing rules. 

I would think transient room mates on renewable short leases would be much safer than bearing the brunt of San Francisco's LTR tenant laws.