@David Cozzi I recommend reading The Millionaire Real Estate Investor by Gary Keller and Never Lose a Customer again by Joey Coleman.

They have more to lose than you do.

Losing the cash flow on the higher mortgage payment, or the new cash flow from another deal?

They do not take responsibility for anything that will cause them to lose money.

If it's been a while is it worth losing this tenantship due to one rent?

Or, more likely, you'll lose significantly more than 10% by making mistakes as an amateur.A large percentage of the people I manage for were managing homes on their own before hiring me.

I don’t really want to lose him as a handyman as I have heard great things, but I fear he may not want to work on the house if he “fell in love” with it and then told he can’t live there when its done.

The Leap of faith.

Perhaps start with a small amount of cash and move up until you have her interest -or lose yours.

in almost all states a PM must be licensed and the rent money must be in clients trust account.. violation of client trust account will cause PM to lose license.. that is your threat.. and its free :)