I provide tenants with a form to request any improvements and it spells out exactly what they are doing, what material will be used, who will do the work, who pays for it, what happens to it when they leave, etc.

For example, in Florida, a landlord only has to give 3 days' notice to pay (excluding weekends and legal holidays) to the tenant, but the Zillow lease provides for more than 3 days.

Do you pay the heating/cooling or do the tenants pay those utilities?

How can I confirm that the tenant is paying on time and properly maintaining the property?

And if the right property is purchased you can recoup the money to pay back loan and any other start up costs to repeat the process.

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.   

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.  

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... 

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

I'm assuming these organizations would pay far below market value for land, but there are obviously also some significant tax benefits that may potentially offset the "lower-than-market" valuation you may receive when selling to them.