It's generally true that a larger sqft house will sell for lower $ per sqft than a smaller one but there are many other factors in each individual house to consider.   

(P.S. we are both young, ambitious, college-educated individuals who will surely add value to any investor in the Chicago area.

O'Diah  How much can you rent the individual units for? 

I have read dozens of post on here that suggest strategies such as financing as individual and then quitclaim back to LLC.

You can meet some here on BP but I'd recommend going to a meet up in your area and chatting with some individuals.

I have Carry Forward Deductions from the 2008 Crash, enough to make all my Profit, Tax-free as I do not have the $3000 Individual Deduction Limit.

Seems that more people than not have their license so most recommendations were of individuals’ family members, not so much good companies to work for.

I've learned how to find deals that not everyone else can because I am willing to go the extra mile for individuals that believe in me.

He does use the BP calculator but I highly recommend sticking with your own spreadsheet because this forces you to fully understand the individual numbers and how they interact.

Typically Single Member LLC activity is reported directly on your individual return for Federal income tax purposes (assuming you haven't made an election to treat the LLC as a C Corporation).