Like any hobby the more you get 'into' it the less the 'cost' matters. I started with a lee loadmaster and have added a few things, a chronograph (highly recomend every handloader get one).
I avoided a dillon because of the initial cost - a 650 runs $750 locally and I'm sure there are things you can add to it.
A fellow shooter has a 1050 he bought for $950 in 2001. Toolheads are not cheap and that's his one complaint. But it's motorized, can pump out 1200 rounds an hour and all you do it keep the primers/brass/bullet feeders full. He spends 2 days in the winter reloading for the season...12-15k rounds. He's easily saved the price of his investemnt 10 times over.
The 1050 can also decrimp mil brass on the fly, trim rifle brass on the fly too he tells me. Yowsa! I know what I want when I grow up!
I advise against the lee progressives, but that's based on reviews, not first hand experience.
Loadmasters (and I suppose the pro 1000 as well) are good presses. There are a few 'user' issues - you must mount to a SOLID bench. You can't go too fast. You have to get it set up correctly. You will have to inspect your ammo and will have tipped primers at times.
However, you can be up and running for $350ish and make 300-400 rounds an hour with about a 3% reject rate (i've had higher and with my latest bench reinforcements I'm at 1% rejects due to primer issues).
Talking with dillon owners (in person, including a commercial reloader) they're not perfect either. No machine is. Each has it's quirks.
It's very difficult if not impossible to get a double charge with a progressive press.
How much do you shoot, and what do you shoot and how do you shoot? Benchrest rifle will require different things than IDPA.
I've started loading 30-06 on a single stage for a couple of autoloading garands for CMP matches. That's different than if i were loading for a modern bolt rifle for hunting.
When I shoot my rifle I may fire off 20 rounds, 60 max. Pistol...200 to 300 on a typical range trip.
With the garand greek surplus ammo is 50c round. Hornady from CMP is $240 for 200 rounds. I spent $305 and got 500 brass, 1000 bullets, 8lbs 4895 (enough to do 1000 rounds) and 1000 primers. for about $60 I got the dies and primer/sizing tools.
So I spent $360 and will have 1000 rounds, vs buying 1000 at $500-1200.
The savings on that alone could just about pay for a dillon 1050.