You need to pull a permit, then the Contractor has to take down the coping and bond beam a couple feet, then core holes in the pool floor (so it wont ever popout of the ground).

You are digging yourself a bigger and bigger hole each time.

Then you get down the rabbit hole of integrating platforms and automating your workflows which takes a lot of massaging and some technical skill. 

I know it sounds sketchy, but I don't know anything about the business and quite frankly if I were to just go at it alone I would more than likely miss some things and find myself in a hole.

Or are we talking holes dug everywhere, plants/ shrubs killed, no grass just bare dirt?  

Of course there is the rabbit hole of owner carry options too, but the above is the most straight forward option. 

Murphy's Law or a hole burning in your pocket? 

Settling / drainage - Gutter set up, gradient of surrounding land, how water moves during rain and subsequent cracks in/around house3.

The contractor had left and didn't monitory drainage.

I understand the rules for a cash out refinance and regular refinance are different but would you just consider this a "loop hole" to get your 75% LTV and not worry about seasoning?