Another unintended consequence would be a plaintiff attorney is trying to decide whether you have sufficient assets for him to pursue a lawsuit.  

.$100,000 - $300,000 is standard and sufficient but talk to your insurance agent and they will help you get clear.

(My current real estate attny is not sufficiently versed in newer tax law to make this determination without input.) 

Originally posted by @Angelica Rose:Can one use a guarantor in the same way that you would to rent apartments with less than sufficient income?

Operating legally is definitely not a safeguard as I provided data to the city that was sufficient to demonstrate that it had operated legally at least the last 5 years (but it has operated legally 23 years) to get maximum STR lottery entries.Note this quota occurred after the council initially passed a ban on STRs all together and pulled the regulation when it qualified to go to ballot (council must have expected they would lose the ballot initiative why else pull it without having it go to vote). 

It was sufficient for its purpose but will not provide me with any additional equity with the bank down the road to be used as leverage for the future.

I would like to see if it is possible to scale using only conventional financing, and home equity loans, in order to maximize self-sufficiency with respect to financing. 

Your basic insurance policy with $300,000 in liability coverage should be sufficient in 99.999% of all lawsuits.5.

If you have sufficient income to max out your fica/se tax, then its really not "hurting" you. 

I was thinking perhaps good locations with a decent amount of properties would be sufficient. given that I was bringing in enough to make sure that I could pay everything off yearly and pocket a few thousand for savings or renovations.