Guitarman- Did you mean the Inside Passage? If so, where do you start and how far north have you gone? I'm planning on running my Wesmac up to Kenai, AK; so I would like to speak with some guys who have run from Puget Sound to Juneau. Where abouts in Montana are you? I've been all over the state, have family in Bozeman, been there more times than I can count. I think if I was trailering a boat around, I would look at a 26' Tollycraft. Seasport and Osprey also build sweet 28' boats that are about 9'6" beams, but they would be expensive and they have outdrives.
I think the 29' H&H would be a good boat, overall length is 29'8" and has a 10'8" beam, so all you need to transport is an overwidth permit in each state you pass through, no flag cars required. Depending on what speed you want, I would go with about 300hp - 350hp and you would have a great, efficient cruiser. The 28' BHM also seems nice and has great lines. Wayne Beal also has a 28' boat and I think Mussel Ridge has a 28'.