What mistakes are Bob and Sally making?

Trying to use time-management tools to solve a motivational problem. System-1-wanting to do something, having pleasant emotions attached to it, feeling motivated etc is a separate issue to efficiently executing that thing. Anki Cards and pomos are not tools which will make your system-1 want to do something.

What would you change, so turn those mistakes into successes?

"How to make your system-1 want to do something." is a million dollar question. The specific case of "How to make your system-1 want to look for jobs" is something that I am currently (somewhat) struggling with, though I definitely find that focussing on just getting started at a task and removing distractions really helps.

You probably also need to do some soul-searching about where you see your life going, what you will achieve with the money from that job, etc. I think that has been a reasonably good motivator for me.