Are you looking to make being a chicago real estate agent your full time job or just a side gig while continuing to work full time? 

And, if you look in the fine print of your Solo 401k paperwork, you'll likely discover that their role is, technically, less than nominal. 

If your new LLC is a disregarded entity (single-member or owned solely by you and your spouse in a community property state), it won’t trigger a taxable event, and you’ll continue reporting income on your personal return.

Talk to a CPA to see how each scenario plays out.A 401K continues to grow in value, but what do you live on? 

All the major PMS platforms have hundreds of reviews on there and you can get a great sense of what will and won't work for you without having to sit through 5 or 10 sales demos.I discovered both OwnerRez (for our STR) and ThinkReservations (for our hotel) on Capterra.

If you discover in a few years that your original title had a problem, your LLC has no recourse.

Are you looking to continue doing the BRRR method or branching out? 

Very solid market, been investing there over 10 yrs and the rents continue to climb! 

I have had houses that I love and want to continue to own.

Its all a learning process. if they can continue to pivot and make adjustments, when necessary, they will do wonderful.