Root as soon as possible. There is no reason whatsoever to wait. Using a stock Droid is a pain in the tush, and I don't know how you can stand it, personally; there are endless ways to customize your Droid if you root, and there is no rational reason for not rooting RIGHT NOW (as soon as you can block off some time).
Even with the OTA 2.2 update, your Droid will run much more smoothly and a lot faster rooted and overclocked. And unless you root, you won't be able to use any custom themes. A stock Droid and a rooted, overclocked and themed Droid are two very different devices indeed.
If you root, you will find yourself addicted to flashing new roms, kernels, themes and basking in the sheer awesomeness of your Droid's performance.