If he works outs well, perhaps move to paying per task/job.I would make sure to have an independent contractors agreement (ICA) signed, ensure that he has insurance (at least liability) and get him to sign lien waivers upon payment.If he doesn't have workers comp insurance (and you don't want to get it to cover him), I wouldn't let him do anything that is "high risk"...

Make sure you have several months reserves to cover payments since anything you do will potentially affect their credit.

Im working towards having my rental NOI cover my  personal monthly expenses. 

We already pay a higher rent rate then our BAH covers.

Get a contract to cover your time and resource to "lay the foundation."

I cover Texas.

Looks like it is a fee the sellers usually covers and the items found on the inspection have to be completed by the buyer on a certain date.

While we certainly have the new property insured because it's primary use is for short term rentals my primary insurance company won't cover it.

Seller will not give enough to cover expense.

If you're going the umbrella insurance route, make sure it will cover you for several things including just the routine slip and fall.