Once we get the head count we can try to find a location to meet at.  

We have a goal of owning enough real estate (buy and hold) to provide a middle class family living so he can retire (I own my firm and my office is in our home so no retiring for me).We have just jumped head first in to real estate investing with our fingers crossed and a ton of prayers said by purchasing a commercial parcel in Ocean Shores which we are designing a multi-family rental for and purchasing at auction an occupied single family home (I'm still cringing).I am slowly learning as I've been "trolling" this site for a couple of months now. 

Notes do not count as real estate even though they may secure real estate.The good news for you is that there are some other options that the IRS considers to be "like kind" for investment real estate that might work for you.  

With experience most bankers will count income from new acquisitions in your business income.

I cannot count how many times I've been owned by internet sarcasm and gotten pissed over things that weren't intended to be rude in any kind of text message.  

When you say Chicago, do you mean downtown or are you counting some of the areas that are part of Chicagoland but not technically Chicago.  

or does different lenders count the 10 differently?

Cross your fingers.

As for being afraid to cross lines, I offer my personal perspective:Sometimes, you'll find that you will have to ask for forgiveness and risk paying a small price.

The town has a solid working class, but I'm not counting on the town growing particularly quickly, so I'm not counting on appreciation.