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

Looking for a professional opinion. 

Addtional Insured status for you on the SL's Insurance policies (General Liability, Professional Liability, Workers Comp., etc..)2. 10 day notice of cancellation from the SL's Insurance carrier3.

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

See Real Estate Professional under Activities That Aren’t Passive Activities, later.

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.

Those areas have higher rents, lower vacancy and higher appreciation.If you manage class A or B assets it’s not awful as most tenants are not professional tenants trying to live rent free for years.

Professional property managers are skilled in market analysis and can help set rental rates that attract tenants while maximizing profitability.Tenant Retention: Good tenants are a property owner's greatest asset.

Starting out with hands-on experience is a fantastic way to build your skills, and I'm sure many investors would value your help.

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