Another hurdle you may run into is that the banks would look at the ownership structure i.e. if it is 100% by a foreign shareholder it makes things even more difficult so they tend to look for domestic owners/partners with 81% ownership (this however, can be changed based on your operating agreement)- not a legal advice just purely from a discussion stand point. 

But even if you made it over this hurdle, the next problem is finding good comps to support the sale price.And to think: I expected this to be a relatively clean deal!

It is not unreasonable to ask for suggestions of standard materials & material suppliers that are included in their budget.  

We've started looking into several neighborhoods, but would love to hear from the community on any key hurdles or prioritized areas in the borough.

There is actually good fun to be had with unwelcome callers; If it's one particular wholesaler, pick an unreasonably high "make me move" price.

Right now, the biggest hurdle I have encountered is how to assess supply and demand for rentals, both long-term and short-term.

but I don't really want to risk going through a tough escrow with a novice buyer trying to shave me down with contingencies and unreasonable demands related to inspections... especially in a softening buyer's market. 

People suck, they are dumb, they are stupid, lazy, egotistic unreasonable, Stobborn, stink and... they are extremyly friggin DUMB!

Expecting an A class tenant in a crappy apartment would be unreasonable.

This is really the biggest hurdle that most people never cross so pat yourself on the back for getting into the game!