Here’s a breakdown to help you navigate your first deal, incorporating advanced strategies, including 1031 exchanges, to attract a broader range of investors.Neighborhood Recommendations: Chicago offers a diverse range of neighborhoods for different investment goals:Wicker Park & West Town: These areas are known for their strong rental demand among young professionals and offer good potential for cash flow.Lake View: Ideal for attracting tenants who want to be close to downtown while enjoying local amenities.The Loop: A prime location for high-income renters, making it an attractive option if you’re planning to house hack and generate a steady stream of rental income.Property Types: Opt for properties that align with your investment goals.

Pros: Diverse job market, low unemployment, great resilience during recessions, nice appreciation, 1% rule can be hit if you look hard enough, great economy, good schools, Midwest nice.Cons: Extreme weather at times (hot/humid summers, tornadoes/hail, brutal cold in Jan/Feb), high insurance premiums, property taxes also really high.

We have the most diverse neighborhoods and each has its own unique investment benefits.

I like working with a diverse group of honest people and giving back the knowledge I have learned around the way and to share with others.

It's so great to see someone with such diverse experiences in real estate here on the forums.

But from an investment diversity perspective, Its never a bad idea to diversify."

University of Illinois Urbana-Champaign (UIUC) has seen record enrollment in recent years: it set its highest attendance in history, with over 57,000 students enrolled and in 2024 just had highest freshman attendance in history and keeps growing, Carle Hospital, Craft Factory (Warren Buffett approves), etc for diversity of economic drivers.

They will be looking at crap dollar store type properties and other junk not worth anything.DST's can give some diversity.

Miami has a diverse market, and many buyers might actually appreciate the mixed-use neighborhood. 

I plan to create a diverse portfolio by some point in my life but feel that the best investment so far to start in is real estate.