Routine selling expenses such as broker's commissions, title insurance costs, escrow fees, recording fees, exchange fees, and the like are permissible 1031 Exchange costs and can be paid out of the 1031 Exchange proceeds. 

Although I only do inspections every six months, no judge would prohibit routine maintenance on a rental. 

I would start out small by giving him routine odd jobs and do as you say, pay them on a per item basis right there on the spot.

That is a pretty routine procedure for just about everyone I deal with from wholesalers to realtors to homeowners. 

I imagine families routinely move in, and are pulled in by boosters.Always been an idea I had.

I enjoy repairing and updating our own home so I think with my wife managing the properties and me doing routine maintenance and small projects this could be a good fit for us and a way to generate some passive income and build wealth over the long term.Thanks for the read,ScottP.S.

people living under the same single fam roof/dwelling don't routinely collect RENT from the rest of their family as  LANDLORD-TENANT relationship(s), even if it is their MOTHER IN LAW =Dthus, while the house may have a grandfathered (or grandparented to be more PC?)

when i moved out here from the east coast, i was relieved to find that most tenants routinely are expected to provide their own refrigerator and cooking appliances!

The only permissible expenses that can be paid using proceeds from the sale of your relinquished property are routine selling expenses. 

They have become a morning commute routine!