We just got back from the trip, so here's a review of (perhaps) the more interesting parts: the rough weather bits. The first 2.5 days, we anchored at Presque Isle Bay on Stockton, and then went up to tour the Devil's Island sea caves the next day. It wasn't exactly calm, but 5-10 knots from the east (forecast: our wind instrument died most days after 10 minutes or so) was fine for using the dinghy to explore the sea caves. When I went in the dinghy, I did give control of the mother ship to some only moderately experienced crew, but they did fine, basically just shadowing us in 30' or so of water off the island.
After 2 dinghy trips, we anchored on the W. side of Raspberry island and dinghied ashore for a tour of the lighthouse and a hike. The 3rd day, we anchored off of Oak island, and took 5 of the 6 of us ashore in 2 dinghy trips for a long hike. All this time, the forecast and (as far as I could tell with no wind instrument) the actual weather was 5-10 from the east. As we returned to the dock, I was surprised and somewhat concerned to see that the wind had changed to the SW and gotten quite strong. The dingy trip back was really wet and a bit exciting: I ferried both parties. We were then scheduled to return to the Port Superior marina to swap crews out. The wind instrument worked for a couple of hours, and showed that we were bashing straight into 25-29 knots apparent: rather a wet ride, with spray washing up onto the dodger. This wind shift was not in the forecast at all, but it definitely caught my attention.
With the new crew, and with winds forecast to pick up (eventually) to 15-20 from the west, we made a beeline for the Devil's Island sea caves, hoping to have the second crew get to see them the first morning before it got too rough. By the time we got up there (a nice sail on and off), it was looking a bit sketchy to have the dingy in the caves on the west (weather) side of the island. So I diverted around to the east side, and let them dingy over in the lee of the island. I told them to turn around when it got too rough, which happened at the north point, as I had expected. It went well for my (~30 y.o.) kids!
We anchored for the night in the protected cove on the east side of Rocky Island, with a forecast of 15-20 from the W and NW. South Twin Island gave some additional protection from the lake to the east of us, so it was pretty reasonable overnight. We did experience another completely unexpected sudden squall from the west just after we had climbed out after a swim off the stern. Really strong winds and rain for about 15-20 minutes. I guess the forecast weather is "just, like, your opinion, Man..." on the Big Lake, to quote the Dude.
We bashed though the waves the next day over to East bay on Sand Island for a rather rocky overnight anchorage the next day. Got in 2 trips to the sea caves over there (at least part of them), and had our first experience of the famous biting flies of the region, but just in the dinghy for some reason: no problem at anchor.
Anyway: it was a really nice charter, with just enough rough weather to get my attention, but not so much that we didn't have fun. (One person was mildly seasick, but no barfing, thankfully.) My wife wants to move to Bayfield now...