In theory you could approach the neighbors before going under contract but they will take your inquiry more seriously if they know you have skin in the game.

Would depend on if you have enough skin in the game or other collateral

Military and am currently working at the worlds biggest surface coal mine.

Insurance has no skin in it since they don't cover mold, only have duty to defend. 

On the surface it may look bad, but my portfolio is pretty solid for only house hacking.

You must have thick skin and the ability to laugh when things seem like they’ve gone wrong.We know there are more than 15 things you need in the home, so comment below of there's anything you would add to the list.I CAN HELP with a a few of these items too!

Should I insist he put skin in the game up front as well and we both take our chances on losing money?

In your Bylaws and Declarations should be a description of the boundaries of your unit (ie, your unit begins at the studs, at the unfinished surface of the walls, etc.). 

You're the one with skin in the game here.

And with all things considered, I would want someone to have equal amount of skin in the game.