And also the local job market.

This is probably a question for your personal CPA or if you don't have one, paying a consultation fee to a Real Estate centered CPA would be a good investment. 

The thing I'll be changing is the financing I've been doing with a local bank, which has been a bit slow and cumbersome.

@Luke Spencer I am not on the management side but I can tell you it took 2+ years to fill 300 units at one of our facilities and the other just hit 300 units in 12/13 months so it really depends on the demographics, and local housing market trend, the more people moving in and out the higher the demand for storage.I think if you're looking at a saturated market then the upfront cash to turn the warehouse into self storage is not a good idea but then again, maybe those operators are on back roads ( low visibility ) and don't push google ads well.

Are you local here?

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.

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.

Try and join a few local Facebook pages and connect with locals who are in the house hacking business. 

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

I’ll also connect with locals through BiggerPockets or Facebook groups for first-hand insights.If visiting isn’t an option, lean on a reliable local team (agents, property managers) to help vet the area.