I know it will save me some money if he gets it repaired?

If so, go over your comps again and your repair estimates and get comfortable with it. 

It will be worth the cost of getting the permit, having it inspected/repaired by licensed folks, then you can at least say you did all that you could in the event something goes wrong.

So I'm not sure if all the repair is absolutely necessary to sell the house.I'm stuck between a rock & a hard place because I trust them both in their knowledge & abilities.

Where I give him the down payment for instance on a 2,3, or 4 plex and he gets the loan in his name (lower down payment Better terms) and moves in and then overseas the rentals and doing upgrades and repairs.

I did some more research and it looks like in Colorado you can charge them a reasonable amount for the time it takes us to clean and repair which we definitely will do and if they're not ready for a final walk through(which apparently we aren't required to do) then they don't get one after May 31. 

If it's $20K in repairs, then you might net $61K over what you paid.At $30K in repairs, you would still net $51K , right?

All seem to run the normal 90% of purchase and repairs up to 70-75% ARV and will take first position on the lien.  

The reason I prompt this question is because, I'm looking at a quad right now in the Jacksonville, FL area that appears to shake out to about a 10% ROI and around $134 per door.

If you separate, do you take money out of your personal bank for repairs on the rental or out of the bank account for the rental.