I did it backwards: I started with a Dillon 650 as my very first reloading tool, and taught myself to use it. I'm not particularly mechanically inclined (ask my neighbor), but I worked through the issues. I didn't ask for help, much, but Dillon helped when I needed.
It is pricy, especially to get started, and especially because I like all the bells and whistles. I load .45 ACP, .38 Special, .44 Special, and 10mm in large quantities (1000+) and have caliber change setups ready for each caliber. Changeover takes less than an hour, depending on how recently I've done one and whether I have to change primer sizes. I load mainly in the winter (cooler in the garage), so with my memory, there's a little bit of relearning every year. Also, each year I learn new things. This year I've learned that my machine likes me better when I run it wet (more lube).
The automatic primer filler is cool, and keeps me running faster, but does reverse primers every now and again, especially on sp. I don't really go for speed, but recently while cranking out .38 Specials, I was doing probably 250-300 in an hour, corerecting stoppages and all.
The economy of this, of course, has gotten better and better the longer I've owned the press, and especially because of the price of ammo now - I just feel all snug inside when I see the prices at the stores...
When I accumulated more guns and different calibers that I wanted smaller quantities of, I got a single stage - and load batches of 50 to 100 at a time.
I'm sorry, what was the question? I shouldn't respond when I can't sleep.
Hope this helps. YMMV.