You can purchase the property within the SoloK outright if you have enough or with a non-recourse loan if financing.

Just the other day I saw someone had used black sheet rock screws in the hangers on a brand new deck (non-permitted obviously, and not a single lag or any flashing on the ledger board, and they painted it immediately before the pressure treated lumber had even dried out so that’s going to peal in the first year, at about the same time that those sheetrock screws start to rust lol). 

I would be amazed, shocked even, if a traditional financial institution was willing to lend on a non-habitable asset up to 80%. 

Things that have stood out so far in my research: 1-Close proximity to Metro North (90 minute ride to NYC)2-Vassar Medical Center3-Marist & Vassar Colleges 4- The Walkway over the Hudson5-Restaurants/Cafes/Hotels, etc.Thanks for your time.

It is very seasonal but does very well in Summer and there are a lot of STR friendly towns.I have considered it however my current goal focuses more on a multi season rental and I am also more familiar with the non beach towns.

I suspect it isn't just that they are responsible people, they probably don't want the good credit score to be ruined by non-payment/late rent.

Our commercial loans are also with them so it would be great if all of our loans were in one place, but in order to refinance all of our loans with them now I’m guessing we’d sacrifice a few points on some of them and have higher payments impacting cash flow not to mention a lot more interest paid over the term of the loan which makes refinancing a non-starter unfortunately.

Institutional lenders will look at your non/short employement as a negative. 

$300K is a lot of credit card debt and probably didn't happen overnight (unless it is medical bills). 

We put $75K down to begin with and likely have $85-100K in equity ( depending on what non-scientific source you check since I haven't had a full appraisal done) on it.