You had an opportunity to demonstrate to BP your detailed knowledge of the loan origination process and through that educate people on your profession.

It will help you find opportunities that are overlooked by others.

Not saying don't consider the options you have but stop trying to analyze too many options though and take advantage of the first opportunity that makes sense that comes your way.

My girlfriend will be attending law school there starting this fall and I saw the opportunity to potentially try a house-hack in the area. 

.), one large reason was for the “underratedness” we see in the city and the opportunity for entering into REI.

I'm excited about the opportunities ahead; however, I would like to avoid any pitfalls if I can.I've already made one mistake and that was purchasing certificates rather deeds (yikes), yet still profitable.Thanks for your assistance.

It is worth considering areas like McKinley Park (right next to Bridgeport and also becoming a Western extension of Chinatown), West Pilsen (still seedy enough to yield an occasional good deal), or Bronzeville (again, pockets of dereliction open up the opportunity to help clean up your own little corner of the neighborhood). 

By replacing UBIT with corporate tax, the rate drop is significant enough that the net after-tax ROI to the IRA may still be favorable relative to other passive opportunities the IRA may have access to.This is not a meaningful strategy for the typical $50-$100K IRA, but for someone with the capital to really do a volume of flip transactions, it can be worth exploring.

I ran the numbers and they showed great cashflow and investment opportunity.

However, the full probates are going to be higher in value so perhaps more opportunity for you to make money.