@Andrew Steffens hit it on the head, in my opinion.

However, with the rates where they are now but likely heading down, I am advising my clients to buy now. 

I would focus on getting that househack first.You can take advantage of a lower downpayment, get a roof over your head, and an investment property all in one.

I shake my head at the 1/4 mile restriction because the idea that you can be prohibited from doing something with your home because one of your neighbors is already doing it doesn't seem right to me.

Quote from @Andrew Steffens: Pricing and multi channel approach is very important nowadays In today's market, I think you hit the nail on the head.  

Chicago for sure has all 4 seasons, but the winter helps us appreciate summer more lolI don't know zip codes off the top of my head, but some of the prime neighborhoods are Lincoln Park, Gold Coast, Old Town, Lake View, Roscoe Village, Wicker Park, Bucktown.Hope that helps...if you want to link up and talk more let me know.

Thanks for the heads up on this one!

Hey there @Hart Turner - I am in for sure.I know for sure that @Mariah Pierce and @Princess Subijano-Cannataro are from Chicago and heading down to BPCON 204.Hopefully, we can get a few others to jump in here, too.Elgin, Wicker Parker, Aurora, Illinois, Logan Square, Lincoln Park, Bronzeville, Schaumburg, Irving Park, Lakeview, West Town, Belmont Cragin

Hey William, I head up EPOC Property Management.

Would probably just do a cash out refinance, some are saying rates to head towards the double digits soon.