Quote from @Lauren Merendino: It helps to really drill down to your goals.

Always good to chat with a CPA or attorney to see what fits your situation!

Pick a lane based on your strengths and long-term goals.

I know becoming a part time agent is one way, but where we live in south Florida seems to be overfilled with agents and I don't think its a great fit for us right now. 

What works best really depends on your goals and risk tolerance, but here’s a quick rundown of what I’ve seen happening in the area:STRs: These are still solid in vacation-heavy areas like Naples, Fort Myers, and the barrier islands.

That will help you garner a better picture on if holding this property longer is a fit for you. 

The one who thinks that they are masters of the universe in EVERY area of life, has 30 different businesses, claims to be fit as a fiddle, with a life in perfect harmony, shows off huge toys, has 30 different businesses, including selling their time by the hour to provide coaching... this person is not running a real estate syndication business.

Plus, very important to understand the new layout and how the dig down will effect the existing stairs, plumbing, etc.Happy to connect and talk through your specific situation because @Bruce Woodruff mentioned every project is different and know one price fits all espeically with these complex jobs.Where at in Chicago is your building?

Main problem is none of the home on market fit our needs/wants.

Give The Ultimate Guide to Grading Cleveland Neighborhoods a read to see which neighborhoods fit your appetite for risk.