Rufo, so you are violating the HOA rules so I don't think they would cover anything if it is the fault of your guests.This will eventually catch up with you and could result in some big fines so maybe think of selling this or converting to a LTR instead.

I'm trying to get a mortgage, but it's entirely possible that the mortgage might not cover 100% of the price of the house.

Oftentimes my initial consultation call with a potential client runs 1 hr and that still doesn't give me enough time to cover everything about the STR market on O'ahu.  1.  

Can try to reposition to Class B, but neighborhood may impede these efforts.Vacancy Est: Historically 10%, but 15-20% should be used to also cover tenant nonpayment, eviction costs & damages.Tenant Pool: majority will have FICO scores of 560-620 (approaching 22% probability of default), many blemishes, but should have no evictions in last 2 years.

That is just example language - you'll need to use wording that is specific to your state - but you get the picture. 

If you have the means to cover debt, you can avoid the accounts being liquidated.   

Picture this, your driving down the road and come to a 4-way stop, what do you do?

More than enough to cover the check written on the undisclosed transaction account.

You'll have proportionally less upside and thus less room to cover errors and overruns on a project with a new team you'll be far away from. 

If you generate enough money annually to dismiss a W2, then consider covering the ever increasing costs of retirement & health care and those do not go at inflation metrics but usually way higher.