Good observations.
Sometimes I procrastinate for weeks about doing something, generally non-urgent, only to have something happen that would have made the doing of it unnecessary. (For instance, I procrastinate about getting train tickets for a short trip to visit a client, and the day before the visit is due the client rings me to call it off.)
The useful notion here is that it generally pays to defer action or decision until "the last responsible moment"; it is the consequence of applying the theory of options valuation, specifically real options, to everyday decisions.
A top-level post about this would probably be relevant to the LW readership, as real options are a non-trivial instance of a procedure for decision under uncertainty. I'm not entirely sure I'm qualified to write it, but if no one else steps up I'll volunteer to do the research and write it up.
I work in finance (trading) and go through my daily life quantifying everything in terms of EV.
I would just caution in saying that, yes procrastinating provides you with some real option value as you mentioned but you need to weigh this against the probability of you exercising that option value as well as the other obvious costs of delaying the task.
Certain tasks are inherently valuable to delay as long as possible and can be identified as such beforehand. As an example, work related emails that require me to make a decison or choice I put off as long as ...
You know what to do.
This thread is for the discussion of Less Wrong topics that have not appeared in recent posts. If a discussion gets unwieldy, celebrate by turning it into a top-level post.