Bought a Rockchucker kit in 1980, first upgrade was to a scale that settled quicker, one in the kit drove me nuts waiting for it. that was maybe 1989 or so. Hornady M scale.
Next was a Chargemaster in about 2011 or 12. No beefs, still have it, working just fine.
Then a Co-Ax in 2012, had always wanted one from day one, not perfect, but, a very good buy. Glad I waited, as in 1980 the Bonanza was still the short yoke on it.
Then I got a case prep ctr in 2013---that was the best investment I've made yet to this day.
I started buying 3way trimmer heads for a couple of trimmers I have, they were not quite as good a buy as the prep ctr, as I still have to use the prep ctr to do pockets, but, still a good buy.
Last big buy was a V4 and the A&D scale, nice, but, only really for satisfying OCD as I can accomplish the same thing cheaper. It's a luxury, like it a lot.
Somewhere around 1989, I bought a Lyman 20lb electric lead pot, that was a very good buy, still running strong, and I've had a pile of use out of it.