A second consideration is that condos locally have become more adverse to rentals. 

Otherwise, if you know any local realtors they can also help see what market rents look like in the area.

I am a local Property Manager and would love to help in anyway I can of youd likeThank you!

If you are in an LLC and looking for better rates and longer amortization terms, I recommend networking with local and community banks. 

I find new lending opportunities by networking at local RE Meetups, Training Classes and real estate functions.   

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

While I’m new to the business, I’m eager to learn, grow, and connect with local investors, landlords, and fellow real estate professionals.

If you're considering mobile homes, the first step is checking zoning laws and utility access since some areas have restrictions.For resources, Mobile Home University is a well-known starting point, and local mobile home dealers can offer insights on placement and financing.If mobile homes are allowed, you could either rent them yourself for higher returns but more management or rent out the lots for steady cash flow with less work.

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.

It is also worth noting that property management is often closer to 30% of gross rent for a short-term rental due to the much more intensive hands-on management compared to a typical 10% for long-term and as such, I agree with recommendations above that medium term rentals may provide the best of both worlds if you are able to tailor proximity to a local need, e.g. hospitals and travel nurses.Again, happy to relay my personal experiences in the area if you're interested.Best of luck,Patrick