The only correct advice is, "Go talk to a professional."

Converting your condo into an investment property and transferring it into an LLC is a smart move for liability protection.You’re correct that retitling the property involves Chicago’s transfer tax, which can be substantial.

Proper research, budgeting, and a well-thought-out strategy are key to minimizing risks and maximizing returns.In the end, BRRRR is an active investment strategy that, when executed correctly, can lead to long-term wealth creation, a steady stream of rental income, and a scalable real estate portfolio.

I would suggest buying without value add only if you were going to keep the property at least 10 years. https://www.neighborhoodscout.com/ca/san-diego/real-estateI think your plan to rent in San Diego is likely the correct choice especially as you get to know the area. 

There is enough demand on the north side you should never have a tenant issue if you do the correct due diligence.Secondly, lots of fake applicants lately.

Of course a visit to the county records office and -correct reading of the legal description would reveal that the tennis court lot was the one being sold.  

I ended up having to pay for their tax preparer’s time to meet with me and make corrections.

Happy to answer any questions about the situation.Please be safe and stay away from him, or any companies he is involved with.I want to make a correction to the original post.

Is that a correct assessment?

If Im understanding correctly, youre buying the home from your mom who will take a first position lien on the property in exchange for carrying the $100k of the purchase price on a private note.