I love how Airbnb just pay me based on the evidence without going through 6 months legal battle or 3 years of collection hunting. 

Yes, there are property management companies, but not sure if I would 100% trust them. 

My retirement system doesn't allow for me to roll anything over given that I'm still employed with the company and also under 59.5 years old.

The specific assistance organization, the screening of the tenant, the property, and the PM company that should be communicating with the tenant all play a role in the success of your investment in regards to tenants.

Holding properties in an LLC (or other legal entity) can offer valuable protection for your personal assets, so I understand why you went that route.

Most are fine with that, but a few will have problems with it and claim there are legal issues, etc..

Anything beyond that is going to take some blocking and tackling (reaching out directly to local companies like solar farms, construction, medical staffing agencies, etc.).

Although for me being one a premier client of our title company they would do date downs for me for free and also keep a running spread sheet for me.

Or for the high-end primary homeowner has no legal way to 1031 exchange; so the deferred sales trust is a no brainer.

Through my studies, I met my current employer, who owns a construction company where I serve as the Sales Director.