Once you have the 44 footer with the big keel for bluewater sailing, how ya' gonna get it from the mid-west to the Pacific. That's a long trailer ride for a big heavy boat. Alternatively, you could go down the Great Lakes to the St. Lawrence and out to the Atlantic, then round one way or the other to the Pacific and on up to the Aleutians. Think of all the duck hunting opportunities on the way--you can make your tender something like a sailing BBSB or a melonseed and build that too!
On your way by I'll host you for a Maine coastal hunt.