So it's pretty risky to put loans out solely on relationship with no skin in the game.

They also use conservative leverage, and put huge skin in the game in every deal (10% or more).

A private lender would be very pleased with that degree of "skin" in the game.  

Even the new drug that they invented like Semaglutide, is working also towards lowering blood sugar.All these from "fasting" to "semaglutide", is just methodology, to lower the blood sugar as main objective.If one is curious on the real impact of it you could  use the device that attach to your skin, to monitor your blood sugar in real time. 

It sounds like if you just structured it giving him commissions it would not really work out considering he clearly wants more involvement/skin in the game on the project.Maybe just split it LLC 50/50 and the commission savings is a preferred return over his split on the exit?

I am finally ready to get out of analysis paralysis and get some skin in the game!

This concerns me as the investor appears to have very little skin in the game.

I would bank on 25-30% of build cost as your skin in the game.

like mentioned above CLEAN  windows seals  PAINT  cracked ( gator skin ) looking old paint    .only one house we replaced all the windows  as they where dated   just make sure you know what the inspector needs and is looking for and you will be fine and the tenets will be safe :)

Hard Money Loan - I do have a nest egg (40K) to put skin in the game along with the majority of it coming from the HML.