Incidentally, I told him that I wasn't going to do any future mortgages for him until/unless he got a damned computer and printer.

Most of the material on the local markets is mostly about Chicago neighborhoods like Pilsen, Printers Row...

There are certain items that I would probably wait to purchase if I am unable to do that (for example, I probably wouldn't buy a printer until either the earlier of 2016 or until I have a property under contract).Thanks for all your help!

You can do a lot of the market for free, just do lots of leg work to get started (get business cards and maybe a printer - $100 all in should set you straight plus gas money).  

8 1/2" X 11" is the standard, just like a piece of printer paper.

You can buy a laser printer, extra ink cartridges and paper for less than $150 all in.  

You could copy them at staples for .10 a copy, or do it yourself with your printer own paper and ink cartridge.

Most managers use Brother printers, that scan directly into dropbox.

Becuase of this we would drive to a property as soon as it hit the market, do the inpections on the spot and then from a printer plugged into our truck we would write cash no inspection offers and scoop up deals before other bids had a chance to ever make it in.  

I'm thinking about the following toolset:HOME COMPUTER  Desktop Computer with 2 monitors, full keyboard, full mouse, printer, scanner, and MS Office Software.