Are  you only  covering Cleveland.

I would take the lower deductible and have the peace of mind that if something were to happen that i'm covered with little coming out of pocket. 

I bought a  5200 square-foot house with a walkout basement that I went out and that covers half my mortgage.

I am seeking to ask the seller to put an escrow with enough fund to cover the cost of all violations and penalty/fees.

The idea is to ease her worry of future increases in her current rent situation by letting her pay what she can afford toward this new house and I would cover the rest.

I ran my electric and drilled my well after getting the construction loan.The bank was willing to loan more than just the construction (to cover a portion of the land), but I decided against this. 

I like multi-units as I've heard vacancies aren't as hard to cope with, especially if you can have the mortgage covered by half or two thirds of the units. 

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.