This feels naive. 2) Do I withhold payment until his insurance company will verify his statement about payout should he vanish?

The structure and roof is good with some issues I want fixed:-covert fuse box to 200amp cb panel-storage shed/garage water damageI’m seeking advice on how to make an offer with either the seller repairing these items (another investor I’m not sure I trust to do it properly) or asking for funds at closing (escrow). 

Hopefully, you were able to utilize a low down payment option to utilize leverage. 

My wife and I are over a decade now collect every payment of rent, never had a missed payment, never had an eviction. 

DSCR loans are based off of down payment, credit score and either actual or market rents so it helps to supercharge an investor's real estate goals and net worth.

Show up unexpectedly and let them earn your trust don't just give it out right away.

Considering we haven't locked down a market yet (debating between Shenandoah or Blue Ridge) would it make more sense to put a set amount in an account for the down payment or bring them a deal first?

Do you have anyone that you trust in that county?

I was able to cover my mortgage payment, cash flow a few extra dollars.I sold my six rental properties in 2012 and moves to Delaware.

Nothing ever came and he has been demanding payment.