Where are you three located? 

Where comps come in to to compare "cap Rates"  (a measure of financial performance) of recent sales. 

If this is your first investment property I'd shy away from HML and look else where.

I’ve seen cases where the lender filed the deed in lieu, then when the borrower threatened suit offered them a cash settlement to forgo litigation.  

Routt County, where Steamboat is, bans STRs.

)  Arizona Arizona is a snow bird state, we have golf, baseball training, then a dead hot summer where nobody comeshow can I come up with some numbers before wasting time to look for furnitures and buying beds ?

Where in PA is the small piece of property you're looking to buy? 

If NY is where you decide to be I would strongly recommend connecting with @Mohammed Rahman he is who I would use. 

Most will have large scale marketing engines where they spend thousands or tens of thousands a month, and operate or license time in call centers.

Step into their shoes, listen to their concerns, and meet them where they’re at.