If you are generally satisfied with your Lee SS presses,
and are cost-conscious, I see no reason not to consider the Lee Classic Cast Turret Press as an appropriate upgrade, or even the Load-Master. With a Turret 4-die setup, you can realistically load 180 rounds an hour with pistol rounds.
Do a simple productivity-benefit analysis of your shooting--i.e., how many calibers, how many rounds-per-month, factor in the workflow issues for rifle / pistol reloading, and there you have the nominal hours-per-month for reloading.
However, it is not my intent here to divert your inquiry, so that's all I will say.
I have seen Dillon presses for sale by some LGSs for (up to) 10% off--but it's my understanding that "the list price is the price" if only because of that lifetime warranty / no BS support.
When you price out the Dillon packages, be sure to include all extras you may need, including their dies as the presumably-Lee made ones may be too short.
I've looked at Dillon presses from time-to-time, but I could never quite get past the cost difference between them and others, and particularly my Lee gear. I guess I am a tinkerer at heart.
Jim H.