There are many people on this site pushing those locations that have not historically kept up with inflation.Btw I advocate all newbies start local even if their local market has not kept up with inflation.  

In suburban Chicago, historical significance or celebrity ties might create a niche appeal, but they won’t necessarily drive up the home’s market value in the same way as location, condition, and local comps.For a short-term rental, though, it could be a great marketing angle—especially if the person is well-known and has a strong local connection.

I am new to real estate investing and looking to connect with any local investor. 

I found this deal from being a local.

It could be worth reaching out to some local brokers to ask them, as they may be able to better guide you. 

The LLC isn't the important part, it's the operating agreement- you should defintiely hire an excellent and local attorney to do that for you.

@Shawn McCormick is local to the area and can share some of his experiences. 

Hey, I am an in the Kansas City area looking to meet and connect with local investors.  

My thinking immediately turned to researching local rental costs per square foot to determine income potential with triple the current square footage.

Buy a used book and find someone local who's doing the thing, and make them your mentor.