Fannie Mae will allow you to transfer the deed to an LLC if you decide to try to go the conventional route, but the loan would still be in your names and you'll need to pay a title company a second time post-closing to do this  for you. 3) I can't speak for the area so no comment there4) If you're self managing, make sure you find vendors you can trust in the area since you won't be able to easily verify if an HVAC guy, plumber, etc. is trying to rip you off and tell you to buy something you don't actually need. 5) Make sure you have clear alignment of goals and a clear operating agreement that spells out what to do if those goals start to not align in the future since you'll be jointly obligated to these properties. 

Now we are in 2025 and although I still own the trucking company, it has been an inconsistent pit that has technically brought me personally no profit.

Unfortunately, the septic company is taking their time, and I’m still waiting for the replacement to be completed.

Office space is gutsy at this time with many companies working remotely, maybe part of your investment was to bet that people will be coming back to work in person.  

Quote from @Dawn Harris: We have a STR managed by a property management company.

The same goes for PMs and companies selling properties.

When they presented the opportunity to me, they showed me what countries want it licensed, what companies are interested and all of that.

In my firm, we underwrite the Sponsor as a company in addition to their individual offerings.

Yet the payment processor is issuing the 1099-K to the property management company.

@Craig DanielsI own a local top reviewed real estate brokerage and property management company in palm bay.