I personally do not shoot enough to warrant a Dillon. IF I were shooting 500 or more rounds a week, then I would get a Dillon, and the cost would be justified. However I dont get that sort of free time, and so the cost is to me, not worth it. I did a fair amount of soul-searching because I really wanted a Dillon setup, but to be honest the value just was not there. Yeah the Lee can be tempermental, BUT I have never seen a progressive press that did not need proper setup and maintenance. Yeah the Lee press needs a drop of oil or two here and there once in a while to run right, and the priming system can be a little touchy, but mine runs great. No issues with the priming system, the powder charging works perfectly and consistently, and I can pop out about 200 or so rounds an hour taking my time, more if I am in a hurry.
I also recently picked up a Lee Classic Turret press and now that I have it setup I really like it. Setup with the Autodisc powder measure it runs great with no issues. I do not use it for prming however, I use a hand primer, only because I have not bought the primer system setup for the turret press. Otherwise it runs great.

I have had several Lee Challenger O-frame presses, and IMHO this is the best value out there. You can pick up the "Anniversary kit" for under $150 bucks and start reloading the day you get it with a set of dies. Its not hard to load a 100 rounds or so an hour and make great ammunition. I still use a single stage press for developing loads when only a dozen or so rounds at a time are being loaded up.