Let them set a month to month lease and then pay you as the cleaner/maid/contact person.

Fee to get listed into the MLS system - why does it cost more to list a million dollar home than a half-million dollar home on a computer database? 

He has nearly 40 years experience and his properties are owned in his personal name.

A 1031 exchange is only an option if the properties you're selling and the property you're buying are for business use (generally, that means they have to be rental properties, used for your business, or held strictly for appreciation and not used for personal use). 

They are not typically designed to create a profit for the person running it, although frequently that person does well on the deals that come through the REIA's membership.

All transactions involving your IRA must be "arm's length," meaning that you or any other "disqualified person" can't be involved directly or indirectly, and that is not the case as you described above. 

The issue we have with some OOS investors is that they never have seen their property in person, they just leave it to the PM and object every repair bill.

I also personally invest in STR's and own one in Traverse City.

That person is brokering without a license.

Ping me if you're personally interested to help shape it or reply if you have features/capabilities you would love to see.