First things first; WELCOME TO THE FORUM!
All the best to you. One thing though; I wouldn't be caught dead living in Chitown!
OK, my experience is mostly with Dillon progressive presses. I started on a single stage and migrated to a Lee Classic Cast Turret press, then on to my Dillons.
I bought 3 Square Deal B presses used. Two from individuals that I shot with, $150 for one and $125 for the other, and one I bought through ebay for just over $200. If it were me, I'd buy one used any day of the week. That is how good their guarantee is. It'll get fixed, no problem.
I also have an XL650 press and I really like it a lot. I am migrating all of my loading to it gradually. In times like these, I have felt the need to get my son and son in law started loading; so I gave them each one of the SDB presses. The press I still have is set up for 44Mag. It works like a champ too!
I have been contemplating getting a Hornady LnL AP, maybe for Christmas! I have heard good things about them but have no experience with one. I have used Hornady equipment before and it is quality stuff, just not their presses.
As a side note; there is a gun store just "around the corner" from Chicago that may be a good place for you to buy your components. It is in Michigan City, Indiana. Kempf Gun Shop is the name. Do a web search, they have a webpage. I am not affiliated with them in any way but they do have good prices and whenever I am in the area, I stop and buy something, even if I don't NEED it!
Hope this helps.
p.s. There are a lot of folks here that use the Hornady stuff. Don't forget to look at the Lee, RCBS and Lyman presses either. If you load low volume, the progressive may not be the way to go for you.