Your primary residence - if you've lived in it for 2 out of the 5 years prior to selling you'll get the $250K/$500K tax free iike @Clint Galliano said. 

Honestly, I never fully understood what they meant—until recently.I’ve been diving into some larger-scale real estate projects, specifically in commercial properties and multifamily development.

Hi Anthony, it sounds like you’re in a good position to start building your STR portfolio, especially with no debt, great credit, and rent-free living!

Quote from @Sarah Kensinger: I love Minoan and HostGPO also, but Minoan is free to use!

HI @Dallas HooverI think the guy/girl you should be looking for is a commercial agent/broker.

I have lots of experience in all types of single-family investing, small partnerships in multifamily and commercial, and a vast knowledge of construction.

Anyways, I might take advantage of the free trial.

If your manager is just 'keeping an eye' on things, collecting/reminding on a few rents here and there and some light cleanup while being compensated in free or reduced space rent then classifying them as 1099 subcontractor is great. 

(Google UBIT or read Tom Wheelwright's book Tax-Free Wealth)Investing actively in real estate through an SDIRA voilates the self-dealing rule for IRAs.  

The contributions are lower so it takes a while to build, but once you do, it's tax-free investing.