I would put a tumbler high on the list, not as important as a press, but I have found (starting off with no tumbler) that tumbled brass runs much better in the press, is easier to resize, and is not as hard on the dies. It also is much better looking at a fresh reloaded box of ammo, and it is all nice and bright and sparkly, and not looking like cruddy.
The-fly has given a good reason why one might own a Dillon. They are good workhorses and if you shoot thousands of rounds every month, they are a good value because you are amortizing that high cost over much more rounds of ammo, and making that many, you can't afford to screw around with a round getting a primer sideways every now and then.
If you shoot more recereationally like me, the Lee gear is good enough.
I would estimate I shoot maximum about 5000 9mm, 2000 .45acp, 500 .44magnum, 500 .357 magnum, and 1000 .38 specials a year. Not including .22's (Which I probably shooot 5000+ every year) or rifle, that's 10K rounds in a good year.
My total investment in equipment includes die sets- some I don't have guns for and probably never will (bought a package deal used)- but I would say with the Pro-1000, the 3-hole Lee turret press, spare press parts, Midway tumbler & separator, two powder measures, a powder trickler, reloading stand and bins, Lee scale, bullet puller, spare turret plates, spare carrier, calber conversion parts, spare powder measure discs and a micro disk & disk doubler, various buckets, bins, bottles and jugs, I have about $600 invested in absolutely everything and from that I can load 11 different pistol calibers and 9 different rifle calibers.
I just ordered components today since I am finishing up a long run to get my personal inventory up to where I want it for the new year.
Cost per box of 50, all using range brass, Wolf primers, Titegroup powder & hard-cast lead projectiles:
9mm Luger: Projectile (125-gr RN) 4.3 cents, Powder 0.7 cents, Primer 2 cents. Total: $3.50/box. Savings over factory: $3.50/box. Annual savings $350.
.38 Special: Projectile (158-gr SWC) 4.4 cents, Powder 0.6 cents, Primer 2 cents. Total: $3.50/box. Savings over factory: $6.50/box. Annual savings $130.
.357 Magnum: Projectile (158-gr SWC) 4.4 cents, Powder 1.2 cents, Primer 2 cents. Total: $3.80/box. Savings over factory: $11.20/box. Annual savings $112.
.45 ACP: Projectile (230-gr RN) 5.6 cents, Powder .8 cents, Primer 2 cents. Total: $4.20/box. Savings over factor: $11.80/box. Annual savings $472.
.44 Magnum: Projectile (240-gr SWC) 5.6 cents, Powder 1.6 cents, Primer 2 cents. Total: $4.60/box. Savings over factory: $25.40/box. Annual savings $254.
That puts my this-year total savings, including buying components, at $1318.00 and I am not a gonzo shooter by any means shooting 10K mixed pistol per year. That's less than 200 rounds a week.