Tillamook can be flat or can be one of the worst. Big thing is the CG will shut it down at a hint of anything. Too many Salmon crazed non-boaters go there. CG is very conservative. If it's open you shouldn't have a problem. If they close it you'll be stuck in the bay with a 1000 of your best friends and all the salad you can eat!
Nehalem is the only other spot (I won't call it a port) North of Depoe until you get to CR. Nehalem is probably the worst bar on the coast. Kicks up at the slightest whim. Jetty's aren't good for much of anything there. Not much fishing is done outside. You are probably better off going out of T-bay and running up (only 10 miles?) rather than plan on trying to get out and back at Nehalem.
CR is big and long, but is not closed down very often in Salmon season. Once in a while it closes to under 30 feet during ebb and until some water gets back over the bar on the incoming. Plenty of 18-20 footers out there (and some real crazy's in 14's as you find eveywhere). The big difference is that on the CR you wil lbe a LONG way from getting inside if it kicks up. Most fishing is done out 6 miles to get off the bar influence and the chop. Fog might be worse there (not sure - I never saw as much fog at T-bay - but it's a different time of year too!). I would not fish out of CR without full electronics (Radar/GPS/VHF and Sounder). I would and did fish out of Garabaldi in a 16 footer with just VHF.
The bar at the CR was a dream this season. Just wasn't an issue. Next year, who knows?
Difference at CR is distance (the bar itself is over 5 miles long on a good day) and company. You can quickly find yourself 12 plus miles from the entrance at CR and not a sole in sight. T-bay the fish are closer, no real need to run that far. Current pushes you south at CR and lots if fish out there too!
Sounds like you need to link up with some company next summer. Be glad to have you run with us if you want to try the big river!