Your answers seem definitive, but I see no reason to accept them as any more than a guess about how certain aspects of human motivation should be modeled.

I've been working on some motivation/productivity systems for myself for a couple years and, after some very significant initial success, have encountered some hiccups. I'm interested in figuring out new useful ways to proceed.

I'm skeptical of some of the "sounds good and/or science-y enough but doesn't actually work" stuff on LW. I was interested in knowing why you think Bob and Sally are wrong in the ways you think they are wrong, and why they ought to proceed in the way you say they ought.

This, for instance, seems too simple:

motivation-creation tools and time-management tools are two different kinds of tools made for solving two different kinds of problems; if you try to use time-management tools for handling lack of motivation, they will break

In my experience, there is a synergistic aspect to using certain time-management tools in order to create generalized motivation. That is, experiencing efficient productivity in something, whether or not it is terribly useful in it's own right, helps to create a motivational energy that can be used toward very useful means.

And in the OP, I see no reason Bob's technique of using ANKI to learn additional languages necessarily could not work if he could find a hack for increased motivation. Yes, his desire to move to France was the original motivation that drove his success in learning French, and now that is missing. But that's where the game begins.

The really interesting question here, I think, is how to create the "artificial" motivation to learn additional languages if you decide that is a thing you want to have achieved. After all, it's not terribly impressive to become motivated do a thing you need or desire to do. The real task is to find ways to do the things that would benefit you even if you don't have a desire for them at the present time.