Hey Zach, If you are looking into DSCR loans to finance these properties, most lenders will require the following: 1.

The overall LTV (including all 3 mortgages) will be key and your selling point will need to be that the 2nd mortgage ($8k) will burn off in 2.5 years (based on your surprise that it was even out there, I'd recommend that you follow up in 2.5 years and ensure that it's been satisified, so that it doesn't surprise you again in the future).Does the $8k grant vest over the 5 years? 

“There were a couple experienced investors on the forums that loved to tell everyone they could manage a short-term rental in just five minutes a week.

Theoretically all the condos have the amenities, not just yours.

Don't forget about single family as well as to cut out 80% of the deals.   

Just know that if you are moving somewhere to chase the hot market, it will only stay hot for so long.

Following!

Hopefully this is not the case where you added the ADU and the value added by the ADU exceeds the cost of adding the ADU.  

I guess VRBO is just being more aggressive on their policing of such shady practices.You just must have gotten caught up in it.

Lease or no lease, you need to follow the timelines that NYS set out from my understanding.