[pcprincipal]

Re: "the problem I've always had with these types of systems is that there's always that one item on your to-do list which ends up more complicated than you expected", I 100% agree. To avoid being subjective like you mentioned, I often prefer to time-box my tasks if I think there's any risk of the scope being unclear. So instead of:

- Migrate photos from iCloud to Google Photos

I'll start with:

- Spend 1 hour trying to migrate photos and write down where I left off

This avoids the issue of being unsatisfied at the end of the day because something didn't get done or something took longer than expected.

If something absolutely has to get done and cannot be time-boxed, I like to veer conservative and either start way earlier than necessary or devote a whole day or more to doing just that one thing (example: taxes - start early, work fire drill - drop everything until it's done).