When do you go meta? When do you stop going meta?

In the video Q and A Eliezer offered some advice about this (the emphasis is mine):

I tend to focus on thinking, and it's only when my thinking gets stuck or I run into a particular problem that I will resort to meta-thinking. Unless it's a particular meta-skill that I already have, in which case I'll just execute it. For example, the meta-skill of trying to focus on the original problem. In one sense, a whole chunk of Less Wrong is more or less my meta-thinking skills.

I guess on reflection I would say that there is a lot of routine meta-thinking that I already know how to do, and I do without really thinking of it as meta-thinking. On the other hand original meta-thinking, which is the time consuming part, is something that I tend to resort to only when my current meta-thinking skills have broken down. And that's probably a reasonably exceptional circumstance, even though it's something of a comparative advantage and so I expect that I do it a bit more of it than average.

Even so, when I'm trying to work on an object-level problem at any given point I'm probably not doing original meta-level questioning about how to execute these meta-level skills. If I'm bogged down in writing something I may execute my existing meta-level skill of try to step back and look at this from a more abstract level. If that fails then I may have to think about what sort of abstract levels can you view this problem on, and similar problems as opposed to tasks, and in that sense go into original meta-level thinking mode. But one of those meta-level skills I would say is the notion that your meta-level problem comes from an object-level problem, and you're supposed to keep one eye on the object-level problem the whole time you're working on the meta-level.

In his discussion post "Are you doing what you should be doing?", Will_Newsome identified what seems to be an important guiding principle of meta-thinking:

Yay for going meta! I should repeat this process until going meta no longer produces time-saving results.

(where "time-saving results" can be replaced with "greater marginal utility" to obtain a form that is more generally applicable)

Some questions we could explore:

• How can you identify when you are "stuck", and when going meta has greater marginal utility than continuing on your current level of thought?
• How many levels of meta can people regularly think on? Can this be extended (via drugs, mental exercises, external tools, etc.)?
• Is it possible to develop a set of meta-thinking skills that help us execute or create Less Wrong meta-thinking skills?
• Should one distinguish between meta-thinking and meta-meta-thinking?

(I plan to try to compile the insights and advice here into a top-level post discussing the principles of, and heuristics for, effective meta-level thinking)

Edit: Changed minor wording and altered the third question posed.