PM cannot make the tenant pay their rent but there should be a process on their side of what they are doing when the rent is not paid.   

Just like you would do with any non-family contractor working for you:- get them to complete Form W9 for you, as you will need their SSNs- have them provide receipts for materials/supplies and keep those receipts- have a written labor agreement (how much and for what) - pay for materials separately from labor- make all payments electronically rather than cash so you can trace them- pay out of your business account, not personal- issue them 1099s next year if you paid them $600 or more for labor (for the whole year, not per job): https://www.biggerpockets.com/forums/51/topics/1167632-expla... 

Is it beneficial and take some load of pressure off your back? 

His long term tenant recently moved out and is about to rent it to his adult son, who will be paying him enough to cover the monthly expenses.  

I pay for the insurance and we all split the bill 3 ways.

However, I'm a bit confused about the process, specifically:Who is responsible for paying the closing costs, and how do you bring it up?

Hi,I did a private lending, term was 1 year. there was a clause that borrowed can extend loan (if lender is ready) for 2 times, each time for 3 months. but borrower has to pay 1 point for each extension(3months). so extension can be done total 6 months.Now, after 1 year, borrower keep paying interest .3 years went like that.Now Borrower wants to pay off. in such case what should be Loan extension point added.Thanks

3) Would it be a better idea to keep the utilities in landlord's name and have tenants pay the bill?

We are seeing if this is an option as we have ourselves in a scaling-up phase - we have purchased a commercial property local to us and are borrowing from our retirement to do so, with the intent of paying back with the possible sale of this home.  

After renting out the finished basement and one of the main units, we'd be paying a very comfortable amount for our part of the mortgage, and upon moveout we'd be breaking even with PITI + maintenance, capex, vacancy which is what we wanted to achieve.