Look around for used Dillons. I picked up a Square Deal (that's right, before the 'B') from RonEgg on here a while ago, I think I paid him $150 or $200. I don't remember. It doesn't matter if you're the first owner or the 4 millionth, or how old your press is, or how many things are worn out/bent/broke, just call up Dillon and they'll fix it up. If they can't fix it, they'll replace it.
For what it's worth, this press sat unused in a box for probably 10 years or more before I bought it. I got it cleaned up with some Hoppe's and some elbow grease, ran it a little bit with no components to make sure it all functioned ok, and decided to make up a dummy round just to check the adjustments. Everything was perfect. All I had to do was fill the primer tubes, pour in some powder and adjust the charge, and I was in business. The little bracket that holds the used primer cup on the Square Deal was broken, I called them up expecting to hear that it was unavailable. I told the guy that I had a Square Deal, and the primer cup bracket was broken, he knew exactly what part I was talking about, and in 2 days I had a replacement in the mailbox.
If you can find a used Dillon, there's absolutely no reason to pass it up. It won't last long for sale, somebody that knows better is going to snatch it.
As far as all the expensive extras go, I thought I was gonna need to get them all in the beginning, but I've never bought any of em. I load 45acp on the Square Deal, and use the single stage for rifle and 45lc. I may ask for a caliber conversion kit for 45lc for christmas, but I shoot so much less of that than the 45acp that it doesn't matter one way or the other. You'll crank out a ton of rounds on a base model Square Deal compared to the single stage, once you get the hang of it, you'll love it. The 550 and 650 may be just a touch faster, but the Square Deal is still more than enough for the casual shooter.