I started w/ a little Lee Reloader press bolted to a 2x4 that I could clamp onto my desk in the apartment (when I got hooked it got bolted down). A collection of other Lee tools; scale, dies, trimmers rounded out the rest of the kit. I didn't know how I would take to it so my initial investment was modest in every sense of the word. I loaded everything on that little press, in between deployments of course, for about three years. Tons of 308 and 223 cases were made to go "boom" again. I inherited an old RCBS RockChucker from the apartment fix-it guy of all people and that was real nice. (and still have it ten years later!) My roommate and I loaded 1K of 9mm on it one weekend. That was tedious but was fun at the time.
The 9mm experience made me want to dabble in progressives. I turned to Lee once again and picked up a couple Loadmasters, one for 45 the other for 9mm & 38 Super. For $300 give or take they were actually pretty good loaders though I never could make the primer feed work no matter what I did. I used one of their handheld priming tools with the primer feed and that kept the speed up. From tumbled brass to loaded round I was still able to do several hundred an hour.
When I started tagging along with one of my friends who does action pistol competitively I was shooting more than I could keep up with. I had always wanted a Dillon since seeing their gear at the SHOT show. Looked at the 650's but then found a great deal on an RL1050 (before the Super 1050) from a Ma & Pa commercial reloader for less than the 650 press w/ all the bells and whistles I wanted; case feeder and all that. Other than one incident with a disgruntled worker, getting parts or conversions from Dillon has been easy even though the 1050 isn't part of their "No BS" guarantee.
If there is one thing that I don't like about the 1050 is that if I want to change over from small to large primers, or change shell plates, I have to darn near take the whole machine apart to do it. What I'm thinking of doing is leaving it set up for small primers, getting one more tool head (almost $200 for the 1050--ouch!) and set it up for 9mm. Those are the two rounds I shoot the most of, as well as my friends that borrow time at the bench. Then I'd like to get a basic 550 that I can set up with cheaper tool heads and still be able to churn out a reasonable amount for the rounds I don't shoot that often. It's hard when you've been spoiled by the progressive!