Back in the 70s my Dad Bought 26ft Bayliner with a Flying bridge and two 170 Volvo Pentas. We always had boats, and a cabin on Hood Canal so he new how to handle a boat well.
The first couple times he took it over the Bar at Iwaco and also out of Westport/Ocean Shores, he would suck in behind the Charter boats and follow them out and back in.
The Bar can get pretty harry at times, we saw two 26 man charters get slammed together after coming out of a nasty swell. We were pretty lucky, even on nasty days, we got through the Bar just fine.
Hopefully someone with some Captain experience of the Bar, will chime in.
Good luck!