This is definitely a loaded question where you're likely to get all sorts of opinions.

I agree that your expected "reloading volume" drives in one direction over the other.
I'm a competitive shooter who reloads a considerable volume so I am very biased in that direction (Dillon 650 for .223/9x19/.45, Dillon 1050 for .38 Super, Dillion Super1050 for .40/.223). But I'm an extreme case. Clearly my bias is Dillon -- I think in the last survey of USPSA Nationals competitors, 85%+ use Dillon presses. More "extreme" cases? Probably.

If I were starting and I thought I was going to reload more than 100 rounds per month, that's when I would start thinking progressive over a single stage. I know there are plenty of folks that load that volume and higher with a SS, I just wouldn't be one of them as my time is too valuable. And, for me, reloading is just an means to an end, i.e., I find no recreational value in reloading other than being able to fine tune loads.

And, cost-wise w/o doing some research, I have to believe that one of Dillon's starter progressives (like a 550) is probably not an order of magnitude higher than one of the nicer SS starter packages. With the 550, you have expandability, i.e., you can add a case feeder, multiple toolheads (one for .223 brass prep in resizing & trimming), etc. So you can easily grow it into a press that is capable of 300+ of rounds per hour.

Another factor, Dillon's customer service is top shelf with any issues.

The add-ons add up too though: calipers, scale, primer flip tray, enough primer tubes, tumbler, media, media polish, brass/media separator...). And all of this is before you buy any of the consummables (brass, powder, primer, bullets).
When I was starting out, I did try to save money on each step but in the long run, I ended up paying more, i.e., case feeder add-on instead of bundled up front, analog calipers but eventually had to have digital (both are cheaper these days anyway), electronic scale (I can't imagine using a balance beam scale any more), at least 10 primer tubes per primer size loaded, two tumblers... Again, my volume is 50K+ rounds/year so all of the little time savers add up for me.
Best of luck. K2