If you are talking about NYC investing, that's a different setup, not as streamlined as Westchester.

I moved here from Florida after doing a ton of research on different real estate markets. 

They may require a foundation (footings) of some sort, a different home set up, among other things.

You might find that installing a mini-split system, properly insulating, and ensuring the finishes match the main home’s quality will make a difference in how the appraiser views it.

Diversifying into different markets, like Omaha or Austin, can help reduce any lender concerns and also spread your risk.Have you thought about the specfic market for your STR or MTR?

The only real problem I ever had was one time I got some tenants who had significant cultural differences than everyone else.

They are good for comparison of different assets and limited in telling you when, where, or how to invest.

Every investor  has a different risk tolerance, comes from a different financial situation and has different financial goals.

Be interesting to see the inner workings of the deal and how it was underwritten.The big question in life, not to be or not to be, not nature vs nurture, no, what is the difference between a HML and a PML? 

I've been at 100% occupancy for my small spaces for the past 5 years.My only feedback is that $2 per month per sq ft NNN seems really high to me, but each market is different.