Thats a tough one. Given that hi-pot tests usually apply much more than rated voltage, it can be somewhat of a destructive test. However, it will definately expose any weak insulation by causing it to fail. The question is, how long would it have lasted without hi-potting given the volts during operation are usually at least half of that applied during a hi-pot test. Good question.
I lean towards a megger test in place of a hi-pot test. The hi-pot will definately verify the insulation but if it is weak at all, it will damage the equipment. In my mind, the hi-pot is just going to give you a warm fuzzy feeling if it passes, if it fails, time for a rewind. Unless its real critical, its probably better to let it fail when it wants rather than hurrying it up by performing a hi-pot. Maybe to summarize, if you have a spare motor around then hi-pot, if you don't then skip it since you might get a little more run time out of it before it smokes.