I use both a Turret and a Progressive--both Lees, BTW, but the brand is irrelevant, I think.
IMO, the issue in considering "multi-die-type presses" is the kind of workflow one wants in 'the long run.' For handguns and semiauto sport / HD rifles) , once one has learned the process, production becomes a very real factor--as opposed to say, the lovingly-crafted hunting or accuracy round associated with many long guns, or with specialty handgun sport niches like silhouette shooting.
If you're going to produce ammunition in some sort of 'production' workflow, then I think auto-indexing is a must. The kind of workflow associated with producing higher volumes of ammo should not require the user to "prevent" the possibility of double-charged cases by having to manually index the cartridge: that is a disaster waiting to happen, for we all have had brain farts.
So, to the point at hand--the Lee Turret (original or Cast) provides for auto-indexing in its 'default' configuration. The auto-indexing can be easily removed--it's a 10-second operation, and the press can be used as a SS (while you are learning) or even manually indexed, as the 550B is used.
Since you are starting with two pistol calibers, I think you are a natural for the Lee Classic Cast--once you have sorted out the process with the press in its SS mode, you can go to manual indexing (a la 550B) or simply go to auto indexing. In auto-indexing mode, one can easily produce about 180 rounds per hour with a Lee 4-die setup.
So that's one opinion. The other I'll offer is that there does seem to be a fuzzy split of "personality types" for which type buys which brand. To that end, my observation is that Lee users tend to be process-oriented and enjoy problem-solving in their goal-seeking; Dillon users tend to be end goal-oriented and find intermediate problem-solving a frustrating experience. I think you need to consider carefully which type you are--as threads about press brands here have shown, there is nothing more frustrating to a goal-seeking user than having to deal with details along the way.
Other factors, such as "quality" cost, warranty, etc., etc. are not considered in this analysis.
And, I will point out that an argument can be constructed for seeing the manual indexing of 'multi-die presses' as a positive. A loader can successfully and safely operate either auto- or manual-indexing machines. However, I don't think that characteristic obviates the benefit of auto-indexing for production-type reloading.
BTW, be glad this did not turn out to be a poll. That feature seems to me to motivate button-pushers and the discussion degenerates into a culture-wars thread, typically carried on between the brand-loyalty posters. In this type of thread, a Dillon advocate has to respond thoughtfully--as the Lee advocates here have done.
Jim H.