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.

Shane is absolutely correct on the premium locations he listed above.

I currently operate a few STRs so have a good understanding of that aspect although they're all located in touristy locations.

Look for a location with low crime, then look for the neighborhoods with the best schools.

I also think of property locations and property conditions having different classifications. 

Investment Info:Single-family residence fix & flip investment. 176 Wildwood Road is a single-family home located in Sag Harbor, NY 11963.

Firstly, it often generates higher rental income compared to long-term leases, particularly in desirable locations or during peak seasons.

@Simon Packman Not sure where you’re located but I have Vermont Mutual in Northern New England for most of my properties and the most I’m paying for any of them is around $4400.

They do not write policies in Louisiana where all of my properties are located. 

CT is 1-2 hour drive from my location depending on the town and is manageable for one project.