While it's a great spot with a ton of tourism unfortunately, it seems the hotels view STR's as competition and have helped to encourage the strict regulations.

If you’re looking to invest in a market close to home, it helps to network with as many local investors as you can.

Can try to reposition to Class B, but neighborhood may impede these efforts.Vacancy Est: Historically 10%, but 15-20% should be used to also cover tenant nonpayment, eviction costs & damages.Tenant Pool: majority will have FICO scores of 560-620 (approaching 22% probability of default), many blemishes, but should have no evictions in last 2 years.

@Samuel Pavlovcik and @Prashanth Mahakali aren't there also some historical watermark records that Chicago keeps that may be of help in @Brie Schmidt situation...

What's most impactful about truly learning neighborhoods is the ability to identify a "C" neighborhood that has the potential or is actively becoming a "B" neighborhood.

Let me know if I can help you expand your portfolio, I work with several investors here in the area that are doing well with Short term rentals!

A great VA will last 6-12 months in a cold calling role.Let me know if this helps.

This helps in setting the right rental prices, finding quality tenants quickly, and understanding local laws.

I am interested in adding to my STR portfolio and helping my family increase the revenue of their existing investments as well!

And it was real estate speculation here that helped cause the Great Depression.