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. 

Look for any clauses about rental caps, short-term rentals, or owner-occupancy requirements.

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

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

This allows us to have a 50% LTV in just a couple short years. 

Long story short, there seem to be huge differences in loan approval processes across the banks...

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. 

If the answer is "close enough," they move forward without much hesitation.While it's true that higher-quality tenants are easier to attract with nicer homes in better areas, I’ve managed C-class properties and had fantastic tenants.

Short Term: No, not happening.