Even hard money/bridge financing will want some skin in the game. 

I guess your "skin in the game" is you purchased the house...

I believe I do trust him, just trying to figure out how to get the work done and him  have some "skin in the game" as well.

You can do it, but you need to be a problem solver have some thick skin, in many cases.Also, in some cases your hands may be tied from a regulatory perspective. 

What would be enough skin in the game to make all parties comfortable in working with a newer player?

They do this on purpose so that:Lenders in general do not like loaning money to people with no skin in the game.

College is a life experience, getting that sheep skin is an accomplishment.

Martin  You have elephant hunting syndrome being impressed with 30 properties which are probably overpriced while the owner is searching for a fool, that's my impression.And, there isn't room from his price to buy and close and resell wholesaling properly but if you try the guru way, that's a big target to be noticed by regulators and a good way to get skinned with a real buyer of a portfolio. 

You may not have enough money to put down for a conventional mortgage but there are many other ways to skin a cat.

Staggering appts w even a small overlap will help reduce your wasted time along with trying to gain a little skin from them, but people are largely fickle creatures.