If you end up picking Westchester and north, make sure you're not too far away from an Amtrak and/or Metro North station as those are crucial for people commuting into the city. 

Maybe if I had a lot of geographically dispersed properties I could take a flyer on one, however I have seen a lot of towns show up on AirDNA list and then disappear.

The loss is typically treated as a short-term capital loss, which can directly offset short-term capital gains, and up to $3,000 of any excess loss can offset other income.Consult a tax professional to ensure you're handling this correctly and maximizing your potential tax benefits.However, if you lose the money you pay to buy the debt, the deduction from the loss doesn't equate to tax savings dollar for dollar. 

I started a business/had twins since inquiring (biz not in real estate) and that has taken up my time. 

This step involves sending formal information requests and setting up meetings or calls to discuss the sponsor's capabilities.

The land lease went up a lot during the time we owned the condo, and we eventually sold it.

My spouse and I prefer not having to split things up and retitle ownership under separate individual trusts.

I just listed it up on airbnb and have had 5 requests to book already - given 3 were for last weekend and I was not prepared for that, so denied all of them and set a 7 day advance notice.

Hey @Anya Boisselle, did you end up purchasing?

Just make sure the OTA backs you up.