The first die set would be a Lee Loader in 12 ga. Dad was the actual owner, he upgraded to a MEC, showed me how to use the LL, and I helped make up trap loads. This would have been in the mid-70's. It still lives with me and even has the crimp starter. I thought I'd lost it until my cat at the time found it in the basement. Apparently they make good cat toys.
The first press was a LEE Challenger 2000. That was a Christmas present in 1988. The last time I used it was to swage the crimp out of some LC brass. It was a relaxing thing to do after shoveling out the driveway this morning.
