They're interested in capital preservation and long term growth.You don't really have to worry about your property losing value in the short run, as long as you have positive cash flow and aren't forced to sell if there is a slight dip.

Running out the cash flow #s then, assuming the 50% role (which seems reasonable given an older home), I'd break-even or lose a couple hundred backs a month.I love the thought of having paid off real estate generating cash flow down the road.

You lose that "one degree" of separation between you/owner and the other side. 

Is there a way to do this so that there is a low chance of losing this inspection money IF I end up backing out on the deal?

In the off chance the lender gets the property they can usually finish the project and break even or get close to it and not lose much.

Ask the REP (retail energy provider) to set you up with a CSA (continuous service agreement) so that when the tenant moves out it will roll back into your name (you don't want to lose power and have to pay re-connection fees, etc.). 

You have the most to gain if you’re in situation 1, the most to lose if you’re in situation 2. 

Best case if you keep the property is that you either lose $150 a month, or break even if you get lucky. 

Should they pay the bill so I don’t lose money

Even at $3k it's probably not worth losing a house sale over.