Find a second job or a legit side hustle, do the work, earn the pay.

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.   

My hope is if it will not give lots of cashflow, at least we’ll cover the expenses and it will appreciate as the area will develop, inflation raises etc.

You are adding an extra expense every 5 yrs to repaint.

I have all the expenses in a different row with repairs at the bottom and a column for each property.There is software you can also use. 

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... 

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.  

Market dependent, section 8 can pay more per month than a cash paying tenant.