That said, I learned how to fly only after I bought a Mooney.
That's friggin' awesome!
OP, good luck with the reloading. I'm at the same stage as you, except that I've not yet settled on whether to get the Hornady LNL AP or an XL650. I too learned progressive on a Dillon 550, and do have a soft spot for the blue machines. I recently tried out the Hornady and it runs very nicely, so the lower cost and lower cost for calibre conversions make it an attractive option.
I hope you've also spent some time loading single stage, and I'll echo the importance of a thorough understanding of each step that others have mentionned. I'm still new, less than a thousand rounds loaded in various calibres, but as long as you remember to take your time, err on the side of caution, and CHECK EVERY CASE FOR POWDER, I don't believe there's any reason not to jump in to a progressive.
I strongly recommend investing in a single stage press anyway though, as I've learned that doing load workup and playing with COL and other relatively small-volume tasks for determining the best load for a given firearm and calibre are much easier on a single-stage. There's less time spent on setup and it's much easier to adjust dimensions when you're only playing with one at a time. This is because until you've got all of the adjustments nailed down, and a cartridge at every station in the press, things will vary a little bit due to flex in the ram/shellplate on a progressive. Eg. you think you've got your sizing length right, then you advance a station and the changing force on the ram as you start engaging more than one die causes it to change slightly and a case hangs up, or is not fully sized. It can mess with bullet seating depth, case bell/flare, crimp, whatever. Expect to go through a few components until you get your dies set for a given calibre on a progressive. I need to get both as I'll be loading pistol on the progressive and using single stage for the .308 target rifle I've got on the way...
For the Dillon, not sure if their case-activated powder measures also expand the case mouth, but if not I definitely recommend a powder-through expander as it will save you a station for a powder check and/or to separate the seating and crimping operations.
Again, I'm pretty new, but these are things I've learned so far, and I'm lucky enough to have a very experienced mentor. Good luck!