Because rates are so low, you could conceivably just keep this mortgage forever (thus avoiding double closing costs), and simply use your other money to buy the next one and the next one.

(In my specific case, it's actually a blessing, as you don't want the laws that I could have conceived.)

Yes you would have to refinance the commercial loan in 5 years most likely but you could conceivably keep adding cash flowing properties onto that original commercial loan whereby it would be one blanket loan and you would only have one payment.

Holding passive assets can technically be done with proper structuring, but it is a poorly conceived strategy.

If our future project are similar to this one, he’d make his money back in 4-5 flips, and we could conceivably grow this business to a point where 25% of profits becomes a very large number year over year.I don’t really know what’s fair here, looking for any advice at all.

The option money along with the security deposit should cover any conceivable damage even in a worst case scenario barring him intentionally destroying the property.Please point out anything I might be missing or feel free to just tell me i'm an idiot for even bothering with this guy.

They seem to have closed just about every conceivable loophole, which leads me back to trying to get licensed, rather than operating on the fringes of the law which could be changed at any time.  

Check out Guerrilla Marketing Weapons by Jay Conrad Levinson, its a short cheap read about every conceivable way he can think of to market products/services.

I'm trying to get in the 'if you can conceive it, believe in it, then you will achieve it' way of thought.

MI also has redemption periods, so it's even conceivable to buy after the auction!