@Jonathan Greene, Thank you for your response and for your professional insight.

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.

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.

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

Hello everyone,I am looking for insight into professional services for property tax appeals. 

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

To me it seems like an incredible pairing, someone who knows and understands to tools available and has the professional ability to leverage those tools not just for tax returns BUT also for tax planning and strategy.I'm a Stessa Pro member and in talking with the pro support team they do not have any preferred CPAs/vendors at this time.Does anyone know of CPAs who know the system?

If you're unsure about the shut-off process, contacting the city of Chicago for assistance or confirmation is a good idea.Has anyone here used a professional service to winterize their property, and if so, was it worth it?

In our opinion, you are hiring us as the professional to find someone to rent to, if you can't trust our judgment than it's not a good fit.I can understand why you would want to have the final approval, trust me I do.

Our local organizations do a lot - we have representatives meeting with council members, a professional PR firm to help change the narrative on STR's here on the islands, and we're working towards increasing our own lobbying power.