change stuffing when needed
As long as you can tighten the stuffing box and reduce the drip to a minimun when the prop is not turning and one drip every few seconds when it is, there is no need to replace the packing. Slight adjustment a couple times each year should do it for most boats. When you repack, it is much easier during winter layup. I strongly suggest Teflon impregnated packing with Teflon lube. I found this almost as good as a drippless stuffing box on my ODay 272. (And a lot cheaper) Seals well, stays cool and doesn't harden like traditional stuffing. West Marine carries it.