I bonus him well and treat him like gold because he takes all calls and completely "owns" the maintenance and troubleshooting. 

@Christina TkacsI think you have to trouble shoot this problem yourself because you have not found someone to help you totally clear it up.

It happens.Explain how to troubleshoot and see if the tenant will help you.

Once the 3 years are over, they will no longer trouble-shoot for that version.Can you continue to use the version of quickbooks past the 3 years - yes.

Manage the construction project - timelines, budget, permits, trouble shooting/solving problems, etc2.

We accept tenant calls, troubleshoot the calls, then dispatch for them if necessary or after the homeowner approves. 

@William C.Hvac installer here, I troubleshoot systems like these all the time.

They have a subscription where it's $35/month for the first home then $10 a home I manage after that with a max 10 homes (which is fine I'm only managing 2). they are offering me:1) They will be fielding and troubleshooting all of my maintenance calls 24/7  2) Guaranteeing $50/hour handyman w/ $50 minimum visit charge. 3) $85/hour for all other trades w/ $125 minimum visit charge. 

Eat the cost, educate yourself, and then you can help the tenant trouble-shoot the issue if it happens again.Many tenants will report that they've checked the breakers and none of them are tripped.

Expenses tend to go down each year as we do major work in first few years of each property (roofs, generators, landscaping, troubleshooting).