We have continued to work with Teresa Fernandez the local go to real estate agent in Coalinga CA.

Are you local here?

In my local MLS, they would be listed in the 2-5 unit category. 

I would love to connect with local investors around the area and discuss real estate.

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

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.

We've invested around $50,000 in improvements (central air and hardscaping) and our mortgage is a 30-year fixed at 2.5%, with a PITI of $2400.We think it could rent for $3,750 - $4,000 per month based on local comps.

My local area has high property tax and makes me wonder about PA as an alternative. 

Sometimes cities will allow this, but it depends on local zoning rules.If neither option works, it might be worth consulting a real estate attorney to explore your options.

You might want to look up the pool requirements for Phoenix and Scottsdale AZ if you want to be the safest you can be, despite the lax laws in other localities.