Quick follow-up, two days in: the approach in
this thread seem to work quite well for checklists. I can just check off the stuff that doesn't necessarily apply for the given day, and everything appears in the correct order again the following day, regardless of whether I checked it off or not.
Also, the aforementioned iPhone app is "Checklist Wrangler" -- apparently "ListWrangler" is just what they mash the name down to so it fits on the home screen.