I found who I thought would be the perfect tenant, passed all of the screenings, met her, multiple phone conversations, everything was great.  

This sounds like the perfect BRRR strategy refinance take some out and then rent it out.

As security deposits are the tenants money, it is not necessarily a perfect solution to ask the seller to cover these amounts, but it also creates great risk on my end if there are no security deposits in place. 

I wouldn't care if people are creeped out, it's about making deals and you can't always do everything perfect to satisfy everyone. 

@Allan Rosenberg,  I think you're asking a perfectly legitimate question: what is their default rate, and what is their uncured default rate.  

Perfect that's right next door. 

Tenent was there and paid perfectly on time before I bought. 

So trying to time your own purchase of a residence perfectly within the span of a couple of decades understandably isn't a luxury that most people have.I'm not trying to discourage you at all from buying something in this area.

A cabin 20 mins from Killington with summer appeal (not far from White River Junction) seems like the perfect entry point for me and quick recovery of upfront costs after a few successful winters and break-even summers. 

It is perfect to cold call!!!