I don't have experience in either of those markets, but I do come from a tenant friendly market (Los Angeles). 

Cash flow is constantly promoted and pushed, and often, the personalities lack long-term experience, so they can't talk about the best reasons we should be investing.  

The student also got great experience and was able to stay in the deal over the long haul. 

And the fact that you have a contractor you know personally is name of the game! 

I have personally invested in these types of properties in Alamance county.If you're open to STRs there's properties up and down the coast as well as lots of mountain vacation properties out West in places like Asheville, Boone, Hendersonville, Cherokee.

Unfortunately, my experience has also been they Sec 8 tenants have generally been rougher on property. 

Personally, I would never open a Series LLC in the State of Illinois.

Anyone has a recommendation for affordable yet experience designer to help with few hours of consulting to upgrade the look of   new airbnb?

There’s so much to learn in this space, and one of the best parts is exchanging ideas and experiences with fellow investors.Looking forward to seeing your insights and discussions here!

Agree that experience is the best education.