Professional SEO here with 15 years experience (who happens to be looking to get into the STR game in the next 12-18 months). 

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.

They often partner with CPAs and other professionals to create strategies that maximize your overall net worth.

Sometimes you have to go with your gut, even your professional agent doesn't have all the answers.

Hi Anna, Unfortunately, this is a common misunderstanding by most CPAs and tax professionals. 

I’m trying to have him see the bigger picture if he puts money in tax advantage accounts first and strategically uses a tax professional, that he will be able to offset his high tax bracket w2.

I teach college level  algebra and trigonometry to high school seniors at Louisiana School for the Blind. 

First page google search has his own website and the "Top 100 Professionals" bio (you too can be a top 100 professional for a mere $5,000, or maybe it is $10,000).  

That being said, a professional is necessary.

Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?