I loaded the first 35 years for rifle and handgun with a single stage Herter's #3 cast iron beauty....that cost me $13 in 1962, and BTW, will still load bottle neck rifle rounds with less than 0.003" runout. Thinking to upgrade my precision, I treated myself to a Harrell's turret, just before the turn of the century ...it's a lovely machine and a pleasure to use, but really no more precise than the ancient Herters. I use them both now, mostly for rifle, but occasionally for handgun load work up.
In 2002, I bought my first Dillon 550B...a truly wonderful press that will easily load match grade ammunition for my short guns at a rate of 200 per hour...and that's taking my time. I was shooting a lot of handgun, and felt that the faster production would help....it did, and I've never regretted the decision.
I load for more than a dozen hand gun calibers, of both primer sizes and decided to buy another 550B, keeping one press permanently set up for large primers and one for small. It's a great set up. Caliber changes, BTW, are five minutes or less....
Dillon in my opinion has the very best customer service in the industry. One call, three rings and a pickup and you're talking with a fellow RELOADER who knows the product and your needs. They're terrific. I'd estimate that I've loaded over 100,000 rounds on those two presses now with only (2) broken decapping pins in that entire time. Dillon sent them along with with their compliments...no charge.
You can also load singly on the 550 or utilize the progressive feature, the machine is easy to use, with a bit of practice once set up. I'd recommend it to a new reloader without hesitation....note that the phone call to customer service is so easy, and they'll straighten out any questions you might have.
Buying the Dillon straight away, you'll never need to upgrade your press short of shooting 500 rounds every weekend in one of the shooting games. But with current ammunition/component shortages, commensurate price gouging, and the insane political climate, that amount of shooting may never come again.
Example: last time I bought primers ~January 2020, they were $32/1000 at Cabelas here in Louisville...not the cheapest place to shop by far, but OK. Since then, primers have more than tripled in the past year and a half...as have most other components when you can find them....best of luck if you're just getting started.
As to dies, & tools in general etc.: Lee is generally ok but not great, RCBS is very good, as are Dillon, Redding, Lyman et. al. If you go with a Lee press, I'd stay away from their Loadmaster progressive...nothing but trouble with the two that friends have worked with; trouble with plastic primer feeds and sequencing. Can't speak to their single stage or simple turret presses however.
HTH's Rod