That is a LONG two days! Did the trip a few weeks ago and we had one day that was 18 miles so we could have a layover day. That was rough. I know a lot of folks can do it in 3 days with little drama. Two is pushing it.
Shiuttle I would use Galice
16' will be fine. We had a couple 15' and it was no problem. It's a little tight in the dory chute as well as dropping in coffee pot, but it is still doable.
A nice spot for an overnight is Horseshoe. Water is low enough you can set up the kitchen right by the water and not pack anything up hill. Get a bear fence and wrap it around your kitchen though. This would make for a really long 2nd day so it is a give and take kind of thing.
Have a great trip!