And also the local job market.

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

But they are usually a bit expensive I believe.I would also go to your local REIA and ask around there.

Looking forward to working and meeting everyone both local and non. 

However, due to high property costs in our local market, we have been exploring opportunities in more affordable states, including Texas, Pennsylvania, Michigan, and Ohio.

Are you local here?

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.

If you don't fall within that category a knowledgeable local real estate agent can be an excellent resource.

But being a local it seems like the prices are only going higher. 

Make sure you check the local ordinances / zoning and talk to the local administrator to see if you can do what you are planning.