Green Water Cruising
This isn''t an uncommon topic, here and at other BB''s, and the snag in your logic is that you aren''t just planning coastal cruising. While most of your itinerary offers day hops or overnights, anchorages in protected harbors & occasional marinas, the Oregon/N Calif coast and the run down & back along the NW Mexican coast is real, honest offshore work.
So first you need to ask yourself whether you set a target for the median somewhere in your boat choice, or whether you try to find the boat - and equip her suitably - capable of handling the worst ''typical bad stuff'' you can reasonably expect.
If you elect the latter target (the prudent choice0, then your price range probably dictates old(er) production boats, which isn''t a bad thing but may look/feel very different from what you picture. E.g. you may be thinking Catalina 30 (which is not suitable for that route, IMO) but perhaps should be considering boats like an Alberg 30 or even 35, a Pearson-built Vanguard 32, one of the older Dutch-built Contests, a Hallberg-Rassy Monsun 31 or an Albin Ballad 30. These were all built in the 1970''s, are all dated, less "roomy" and ''old fashioned'' in looks, are all designed & built better for offshore work than the more contemporary designs, and many have been refurb''d & cruised while doing what you now are considering. You''ll find numerous examples like these for sale, some of them reasonably well equipped, in Latitude 38 each month, just to mention one possible source (www.latitude38.com - they post all their reader ads).
Good luck on the search, and it''s a great trip - except the last part, heading back N to Oregon. You''d be a hero to your crew if you sailed up the Sea of Cortez and used the trucking service to take her back home via the border. <g>