Due to the current interest rates, you probably can't live for free, but you can definitely learn how to house hack in that first year, reduced your personal housing costs, learn the rent by room/co-living strategy on-site, and then probably break-even after move out, but most importantly, it is possible to make that work in 2025 with today's rates.It just takes being open-minded and willing to be flexible for the 1st year.  

We're based in Tampa and, in addition to personally investing, I own a mortgage company that provides financing for tons of investors.

So it's just personal preference and budget for a host.

Not that it cant or wont, but unlikely.If OP applies for homestead on a new property, then I personally would not lie during the application about receiving the exemption on the existing property.

.✅ More Control – You’ll personally handle tenant screening, rent collection, and property upkeep, ensuring everything is done to your standards.✅ Stronger Tenant Relationships – Being involved directly allows you to build rapport with your tenants, which can lead to better communication and longer leases.Cons of Self-Managing❌ Time-Consuming – Dealing with maintenance requests, late-night emergencies, and tenant disputes can quickly become a second job.❌ Legal Risks – Chicago has strict landlord-tenant laws.

This deal proved to be the perfect balance of financial gain and personal enjoyment.

Would you personally intentionally go out and do this?  

He’s not a pushy salesman, and I’ve got a business partner who has worked with him for the last 10 years without any issues.As for your situation, I wouldn’t say it sounds like a Ponzi scheme, but I’d strongly recommend meeting with the fund sponsor in person and asking as many questions as you can.

I’m the last person who should complain about grammar, but these are yellow flags, at best.

I personally like Alabama and Tennessee a lot, depending on what specific area you're looking at.Look for Class B or C properties in stable rental markets, particularly single-family homes or duplexes.