I think it will also depends on state laws and a lot of information not present but the HOA rules and insurances are two different things.

That will be an important piece to this depending on how you plan to source your capital.

Whether the lender decides to do anything, and exactly what they decide to do depends on the lenders particular strategy, target ROI, risk tolerance, current interest rates, interest rate of subject mortgage loan, etc. 

It's not what I would call a super rough, probably different street by street, and would most likely depend on the neighbors right around the property. 

Many of also argued that forcing out many STR's will impact our tourism revenues, which we're very dependent on, as many travelers won't come here if they have to stay in a hotel.

With investor's properties, depend on how risk averse they are, I fall under either just follow their criteria or maybe coach them my insight if I feel they are open to ideas.

Providing relocation assistance to tenants, for example, if I want to sell the property or move back in - this can range from one month's rent to thousands of dollars (e.g tenant has a disability, minor children, elderly it will cost you more), depending on the city.

Expect rates to be higher than "typical" financing programs - right now, I'd plan for at least 8%+ depending on the whole scenario. 

All depends on what your goals are and what market fits your game-plan/criteria 

If you're only using a portion of the funds, its less of a risk and could make sense depending on your situation and the deal itself.