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It just isn't worth it. Lets things come naturally. Improve your sites on a steady basis - and you will at the very worst - miss one update.
The amount of time spent tracking googlebot and the like just isn't worth it.
Only if you have to make a decision should you strategize about this type of stuff.
For example - if you (for some reason) get monthly updates from somewhere and want to pick a day of the month - then fine. But don't change YOUR schedule around to suit google.
Google can change anytime - be flexible.
It used to be useful to time your listings in certain directoryies to be in the "new" category when googlebot came around (for several reasons including PR).
It just isn't worth it anymore. Google seems to be moving to a much more fluid way of doing things.
It is like timing the stock market now - good in theory - but VERY hard to do in practice.
Spend your time on other things.
It is harder to track things - as the cache used to be when stuff was last pulled and things like that.
Best thing I can suggest - is to get things up real quick after the update - but I am not sure if that is even valid anymore.
And with the way they are changing - I wouldn't place any bets that you can predict things like this anymore.