It all depends on your money supply, I guess. I'd check gunshows for a good used RCBS press, the fully enclosed, not a C-type. If there is no wobble to the ram, it's as good as new.
I'd buy carbide dies, since they'll be appreciated by your grandkids. If you don't run all your fired brass through a tumbler, you can wipe out "regular" dies really quickly. Lotsa scratches...
If you shoot competition, get a Dillon progressive or equivalent. I bought one of the first Dillon's, and if I concentrate on what I'm doing, I can crank out around 100 an hour of .45 ACP...
You can also find a lot of used stuff of the "thingummy and whichit" sort at the gunshows, usually around half of new prices. Taper reamers, primer pocket cleaners (more used for rifle), case-lube pads, shell-holders...
Used powder measures are okay, but I'd go with a new scale. I'll defer to others' judgement on scales, although I've used most of the brands. I started out on an old Pacific scale where you put the weights in the pan and adjusted the beam-weights for your load. Wuz I ever glad when magnetic damping came along!!!
Loaded a bunch of '06 with an old Lyman 310 "tong" tool.
I guess the key is a lot of caution until you're fully familiar with whatever you decide on. It's real embarrassing to be in an IPSC match and have a round with no powder, in your string. Sure can do funny things on the next shot, too...
If you're a reader, hunt up the 100-year old book by E.B. Mann, "The Bullet's Flight From Powder to Target". Read up on some old-time target shooters like Harry Pope, who's said to have used only one cartridge case, reloading for every shot. He was known as "The Human Benchrest"...
Another old book for some historical perspective is Phil Sharpe's "Complete Guide to Handloading". It gives a detailed view of the world of reloading in the 1930s-1950s.
Best regards, good luck, and good shooting!