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Have you come across any calendar software that will do this automatically? iCal will let you do the 2nd Monday of each month, for example, but I don't see a way to get the 2nd of each month when it is a weekday and some nearby date when it falls on a weekend or bank holiday.

What I do is not bother making it a repeating event, and instead just enter a year or two of them all at once with start dates so I only see 1 at a time, and a reminder action to put in more near the end of the run. Or I enter it as a repeating action (or action group) with a note (or an explicit action) to fix up the date on the next one. Which approach I choose depends on whether or not it might be useful to see a list of upcoming actions instead of just the next one.