Hello Kenyatta, I'm also new to New Orleans and actively getting involved in REI.

Absent them, risk is controllable over time.

They financed 100% of that transaction, and I took on a huge loan - a huge risk for a broke guy like me.

Lastly more to my point - I thought you worked for a MF syndication in the past that I was not sure but wanted to mention and that you are not just someone coming off the street having never been involved in a deal (unlike a lot of others).  

Generally speaking, I think tech like this stuff and social media have lowered the barrier to entry, allowing people to take risks they dont fully understand, whether wholesaling. flipping, lending, etc.

Have you ever done this or been involved in this?  

Personally I think Josh himself is innocent but the company definitely is involved in shady and deceptive business practices.

Converting your condo into an investment property and transferring it into an LLC is a smart move for liability protection.You’re correct that retitling the property involves Chicago’s transfer tax, which can be substantial.

It sounds like you have an un-permitted unit, which is essentially always a risk since there has been no notice to the AHJ that it exists and they can therefore initiate a code case to have it removed in most cases.

Check AirDNA for demand, pricing, etc.The Dekalb Board of Commissioners has proposed regulations for short-term rentals. https://engagedekalb.dekalbcountyga.gov/airbnb-dekalb-countyShort term rentals require you or your property manager to be hands-on and come with more risk.