Don't forget about your property taxes going up to account for that ADU.

Completely agree with the original post but an LLC is NOT a tax vehicle.

Do that every 2+ years, sell tax free, repeat, and you can be set for life ("live in flips"). 

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

A good real estate accountant can save you thousands of dollars by leveraging entity selection and formation, tax deductions, cost segregations, bonus depreciation and tax planning.I recommend finding an accountant who specializes in real estate taxation, business taxation, financial planning and tax planning.You may want to consider working with your accountant remotely to expand your options.I would also recommend looking for a accountant willing to work with you throughout the year.

According to the City of Chicago tax code, it costs $5.25 per $500 of the transfer price.

My overall goal for my professional career is to start an investment firm and own a big multifamily portfolio and get into development.

If you are not familiar with Scott, Scott was the Executive Director of the Opportunity and Revitalization Council, which was tasked in part to support and advance Opportunity Zone tax credits during the first Trump Administration.

I shifted from investing with a cash flow focus to the appreciation and tax benefits side of things.

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