I once sized/deprimed 1,100 9mm on my Rock Chucker over the course of 2 evenings - because I wanted to see how many 9mm cases this one plastic container held. It got quite tedious, to the point my back started to ache.
The following only works if you're not in tight short-term time crunch from calendar/total elapsed time perspective, but I've found doing things consistently, but maybe not in long sessions, helps immensely in getting lots done over multiple days. For example, I wet tumble in the small Harbor Freight tumbler. I can only do 100 cases or so at a time. It is amazing how much I can get done, if I just consistently find windows of time that enable me to start a batch and then get them in the dryer.
So would it help to approach it from the standpoint of "250 cases / night. I'll have them sized, deprimed in 8 evenings." vs "1,000 cases sized/deprimed one tonight, 1,000 cases expanded another night."? Many frequent small sessions vs a handful of "OK...suck it up and get 'er done!" sessions."