Except for some time with the Lee "whack a mole" loaders, I started reloading with a Dillon 550B:
Read the instructions. Maybe 4 or 5 times. Then read them again.
Read the introductory chapters in a reloading manual.
Load a few pistol rounds, using one station at a time.
Read the manual again.
Finally get progressive operation working for pistol.
Try to get grin off your face. (Fail...)
Decide to reload bottleneck calibers, order dies and additional toolheads.
Read the manual again.
Fight headspace, order Wilson gauges.
Load a few rifle rounds, using one station at a time.
Get trim length and headspace figured out, and use press progressively after doing resizing as a separate operation at station 1.
Try to get grin off your face. (Fail...)
Anyway, that's the general idea. Progressive presses are more complicated, but I believe they are not beyond mastery. If you are into details, and understand what the machinery is trying to do, you can usually get it working correctly.
Did I mention reading the manuals?
I believe I ultimately saved money, because I didn't wind up with a garage full of "beginner" presses and tools. However, I will readily admit that, if I'd gotten frustrated with the whole business and gave up, it would have been a more expensive mistake.
So, if you are determined to make this a lifelong pursuit, and if the initial investment isn't more than you can handle, I wouldn't give up on the idea of starting off with a "low end" progressive like the 550B.
Good luck!