You won’t end up in tax court but if you do, you would win based on everything you cited about material participation as long as you have a time and activity log that shows your tasks and provide a guest list that shows the number of nights your guests stay (easily found on the various platforms). 

Reductions in the price of long-standing homes may be an indication of motivated sellers, providing a chance for a negotiation, particularly if Zillow estimates are lower.

There are other types of services a management company may provide you and/or the resident. 

There are plenty of NNN tenant-in-common investment providers out there, along with DST sponsors, deal syndicators, etc.   

@Tracey BondWhat service can you provide besides being an agent?

The investments should be chosen based on increased wealth, so that an investment in land, providing no income, but likely to triple in value in 24 months, would be chosen over a office building throwing off 12% income, but unlikely to increase in value.  

Here's how I would approach it:- Offer the Renewal to Both: Provide them with the option to renew the lease per Nathan's suggestion.

Networking with industry experts can provide valuable insights and personalized services.

These markets often have lower competition and can offer higher cash flow potential.Midwest and Southern Markets: States like Ohio, Indiana, Tennessee, and Alabama often have lower property prices and can provide better cash flow opportunities, even with higher interest rates.Value-Add Properties: Focus on properties that need significant renovations or improvements.

They have all been extensively underwritten and they provide the loan servicing for you.