There's a little bit of a learning curve to using the Zip Trim chuck. Once I learned it, I haven't had any issues.
After the brass falls out, you have to open it at least a half turn farther before putting in the next case (with a drill, that's no problem, just give it a tap in reverse). Then when tightening it, you have to let the brass self-center. You can do that by holding the case against the base of the Zipchuck with just a fingertip while tightening - either by hand or with the drill motor.
It's not color-by-numbers, but once you've learned how to work it, it's not fiddly or frustrating, IMO. I can throw on a Hulu vid and very comfortably churn out ~250-300 cases in the 42 minutes it takes to watch a show with the commercials. I could keep that up for a few hours without any discomfort; it takes very little effort or attention. The only place where I need to actually look at what I'm doing is when getting the tip of the pilot into the case mouth and getting the brass into the chamfer tool. Getting the cases in/out of the Zip chuck can be done blind-folded, all day.
The only thing that I'm bummed about is the Lee cutters don't work so good if your neck thickness varies a lot and you like to trim before expanding. That's a pretty specific set of criteria, but alas that describes how I trim my mixed 7mm-08 cases. I had to sand down the pilot a little, to get my converted 308 cases to fit. And now, with the sloppy fit, it can be a bit fiddly finding the flash hole on my converted 243 cases. I haven't tried deburring the flash holes, yet; I hope that helps.