I feel I have a rough idea, which is..I'm in Rogers Park, my next important step is to wait out 1.5 years until I can fully rent out the condo, but for the meanwhile get a roommate to save more money.

100% leverage, which is what it sounds like you're proposing, is high risk.true private money IMO is someone already in your network - your uncle, your dentist. 

I will be very careful with my first investment if I were you, unless you have a rich father or uncle who is willing to finance your mistake.

This can lower your tax bracket potentially and you earn interest on the income you would have normally paid Uncle Sam.10) At the close of escrow, move funds outside of the taxable estate to avoid the 40% estate tax on amounts over $11M single or $22M married couple.

I spend a lot of time reading these forums plus I've read David Lindahl, Ken McElroy, James Randel, Scott Berges, Roger Dawson, and have been watching videos of anyone else from first time to pros with REI information.

Assorted department head's over the years buying pen's from "Uncle Sal" for $1,200 per pen.

Depreciation recapture is taxed at an investor's ordinary income tax rate, up to a maximum of 25%.Appreciation is taxed, BUT Uncle Sam will allow you to KEEP that tax $ owned as long as you use it to do other Real Estate Investing that meets there guidelines (1031). 

My uncle Manriku.  

The market here feels like it’s on the verge of a shift—many investors who bought in the last few years may need to sell, which could open doors for those of us ready to take action.A little about me: I grew up in a working-class family where I started young, helping my father and uncle manage their properties and businesses.

On the other hand, this phrase is often used by the likes of Uncle G (who, having an accounting degree, should really know better) to suggest claiming personal expenses as business deductions.