Here's an article about a woman who "rented back" an apartment at age 90 and wound up outliving the buyer.

There are crappy licensees and worthless, anti-education lead generators who call themselves wholesalers or investors when their efforts only cause more chaos.

Steady, now.Painting wood floors is not necessarily somehow anti-historical, and would not necessarily be inappropriate.  

While they are not all in Chicago, in this day and age you do not need them to be.

Besides, title companies don't want title search orders, they want closings.Great advice Tom.. my Daddys attorney in circa about 1969 before I was old enough to get a RE license but was around real estate all the time ( my dad drug me to his meetings with him and many were with his attorney)  he said son you want to make it and get ahead of the pack you Learn the court house.. now in this context this means going in and going through the old books and recorded plats etc. in todays age it simply means understanding all the on line tools and what it all means.. this is where the money is made. 

Our buildings are both about the same age, style and condition. 

I started working right around your age.  

I don't know if you can put up how many people can live in the property but you can make it known that any person over the age of 18 or 19 will automatically be placed as a listed tenant on the lease.

The more experience you have in the age of properties, and the things that might be issues- probably the faster you can close a deal comfortable on your side as the buyer. 

If I am feeling anti-social, I look for a few things to get myself warmed up: someone who appears to have a similar personality to me, someone who looks new, or someone who looks more uncomfortable than I am.