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.

This is all great advice!  

@Jeff Nash would be a great resource to speak with on companies/investments to offset your W2.

Quote from @Alex Clark: Looking to buy a property in OhioCleveland has a lot of areas that are great for cash flow 

It's great that you're focusing on ensuring full transparency with your property management company.

Having models is great if you understand their limitations.

Hello, I am looking to sell my rental property and great investment opportunity in Toledo, Ohio.

Just my 2 cents from someone that has both great and not so great properties in the area.

Now some stayed with me and that was great but some learned that with a little bit of knowledge you can do it on your own.  

Great question!