Any recommendations for a good financial advisor? (Chicago or remote)

You may have better luck, and get better advice, from a real estate tax attorney.  Most financial advisors are only educated on stock and bonds, not "alternative" investments, real estate being one.  

You could reach out Scott Jensen.  He is on bigger pockets.

@Ryan Bird

To Pauls point, the complexities of planning around real estate cash flows or more generally the large outflows of an alternative investment portfolio is beyond the scope of many adviser. Thankfully there are some decent advisers on here who are real estate investors themselves. 

That being said, a strong CPA and Attorney team should always be on speed dial in this industry. Happy to refer some of my favorites in the midwest if you need anything.

Thanks for the mention @Randy Bloch .

Most financial advisors don't offer any help with real estate but there are some of us that do. A few months ago I started a study group for financial advisors that work with real estate investors (or want to work with real estate investors). So, there are some of us out there, but we're rare. Let me know if you want to chat. I would be happy to help if you're a good fit or to recommend you to someone who would be a better fit.

@Ryan Bird Financial Advisors come in many different flavors to include compensation structures and areas of expertise.  The core value proposition of a competent Financial Advisor/Planner is helping you achieve your goals in the most efficient manner (ie avoiding costly mistakes) and also to help with specific knowledge applied to your personal situation.

Also, many Financial Advisors/Planners can do business anywhere in the United States through secure and compliant cloud-based client solutions.