Multiple people including myself have tried to caution him of the the true costs but he's been repeatedly dismissive and has made it clear we give him motivation and he wants to prove us all wrong (whatever that means). 

VA loans are the only loans that allow this, and there is no rate penalty for it no longer being your primary home.With that in mind, you could do a cash out refinance today at a higher rate than current market rates which will create profit on the loan, we can take that profit to pay for your closing costs.

Sounds like you need to have a relationship with a couple of good contractors, 40k for vinyl siding sounds high, what was the material cost.  

I am slightly confused about your numbers, though...is the $215/SF the construction cost? 

I had to go that far away due to the insane cost of real estate in Boston, so I fully understand the predicament.

Insurance-  replacement costs.  

In doing so, bear in mind that the cost and admin of a corporation is higher and that the tax treatment is different:1.

.: Cost of risk scenario. 

This can be very expensive and is usually the worst choice because you can't justify the cost.2.

It saved my quite a bit on interest costs.