All but 1 of my trips have involved at least 1 drop-off/pick-up somewhere other than R.H. or Windigo. Getting dropped off is real easy--just have your "carry-on" stuff ready. The crew will pass your packs off the boat to you, so don't all head off immediately (sounds weird, but I've seen it happen). McCargoe Cove is about 2 miles long and a no wake zone, so you have plenty of warning. As far as the pick up--don't be late

, early is good, and have your gear on the dock ready to load on the boat. I tend to get a little antsy waiting, but there's plenty of reasons why it may be late (or early)--weather, number of stops, waiting on other folks, etc. If the weather is bad, it's late, and you're wondering if it's coming or not, make sure you keep your gear at the dock, someone watches, and everyone stays within earshot, even if it's all day. This doesn't happen often, but it can. I once left R.H. at about 1pm instead of 7am because of the weather. The rangers had been able to alert the folks we picked up at C.H., but you can't count on it. All that being said, overall it's been remarkably on schedule for me.
Can't speak to the food drop--never done that.
I've done much more paddling than backpacking, but I do know the hike from Todd to Hatchet is easy--so that's almost like a layover day. And bring plenty of water--2 liters each was not enough for us between Hatchet and CBW. Have a great trip!
24: MB | 22: BI | 21: RH-DF | 18: MC-DF | 17: WI-SB-WC | 16: RH-CI-RH | 14: BI-MB | 13: RH | 12: MC-TH | 11: WC-HC-WC | 09: MC-RH | 05: MI-MB-RH | 02: MC-CH | 01: BI-RH | 79: RH