Do you think he is going to hold over or squat?

I buy 1-2 properties a month for long term hold.

Don’t hold back, tell us how you really feel, LOL  

So after being laid off a few times in the last 8 years I decided to get back into investing but this time focusing on buy and hold multi family real estate so that I could built wealth that could help me retire my wife who just had a long battle with cancer and survived , but is now back to work, and I want to give her a relaxing life free of all the stress of the world (by the way did I mention she is also in the mortgage lending field) so that explains the urgency to retire her from w-2 work ! 

Homes that get more winter weather need a different level of upkeep, but nothing more than a regular home needs that is built for their specific area.

I can build a 1,000 sq ft cabin including land  and holding costs for about 350k or so and the cabin will appraise out for about 500k to 525k and will produce gross rents in year 2 between 50k to 60k.

Maybe you can expand on what kind of properties and price points you're targeting, buy & hold vs Flip vs MTR etc?

If you're looking for long term buy & hold, there's money to be made. - Renting in this area is solid, I've gotten what they call B class tenants and more or less they've been great.

I really feel this financing situation is holding me back from going and finding a deal.

The idea of my credit union where I bank holding these loans and servicing them and never selling them, keeping it as simple as possible is what sounds the most appealing to me after these experiences.