I've been in the habit of upvoting each question I'm answering, but it has recently occurred to me that this may be counter-productive in a collective enterprise such as PSE, since whoever posted the question might thereby be encouraged to disingenuously delay their acceptance of any answer, so as to artificially inflate their PSE reputation. I'm sure I'm overlooking some factor(s) which would discourage that practice, but might it be possible to specify them for me?
You should up vote any question you think deserves an up vote. Usually this is for reasons such as it fits well on the site, it is clear, etc. I don't think there needs to be anything beyond this. We should be evaluating the posts independent of who is asking them and what may or may not happen with their reputation.