If something's truly bad, then sure, delete it if it helps keep things organized. Like if I discover I was out of tune on a take, then no reason to keep that around. I might even use it by mistake somewhere, so get rid of it. But even small snippets, like a false start, I usually don't get rid of. When it comes editing time, it's possible that that one bar I did manage to play is the best of the bunch for that few seconds.
As far as knowing when to stop, I usually try to get at least a few complete takes that I'm pretty sure are good. I usually relax once I get a good take, and in many cases, the ones that follow are better. The challenge is that often when you're playing, you don't know what the good takes are. Sometimes the take I thought was "the one" actually sucks when I listen back, and another that I thought I messed up sounds good. That's a good reason to not do anything rash, like cutting off the last notes, or swearing at the end :-) You just never know.
I've been inspired by the sessions I've done with Steve Baughman. Steve's a perfectionist, and to me, every take he does is a keeper, no editing really needed in most cases, but he doesn't stop with one take, and will do quite a lot. We'll often record anywhere from 5-10 complete takes of a tune, and again, for the most part, I'd release any one of them as-is. But Steve wants most of all to capture the feel he's after, so we'll listen to them all, and Steve will take notes on parts he likes or doesn't as we go, but most of all, he's looking for the take that was the most musical, in some undefined way. We'll use that one, even if it has even some blatant mistakes in it, and use that as the base, fixing small parts in the comping if needed. Usually there's a take or 2 that Steve declares "perfect", but that he thinks sounds less musical - it's easy to play stiffly when going for perfection. So those get ignored, in spite of being flawless, in favor of whatever one he thinks flows the best, musically.
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