I've crossed the bar numerous times in many types of boats including square stern, small rudder slow boats. The general concept is the same no matter the boat. Lots of small slow boats cross the bar all the time. Preparation and timing are key to doing it safely.
- Best to cross in light winds and low swell. Watch the weather predictions for wind and swell, generally mornings are lighter winds than afternoons.
- Flood tide is best when crossing inbound. Slack before the flood best outbound. You can cross outbound on the flood but it will be a slow trip.
- AVOID ebb tides and onshore winds. The seas can stack up close together and breakers are common. On some days the change from benign to deadly happens almost instantly as the ebb starts. Especially with an onshore wind.
- Stay away from Clatsop Spit and Peacock Spit. Both can be boat killers.
I have to say this, you may already know it but I've seen too many people get bit in the back side for not understanding this. Tidal current predictions and tide height predictions have very little time relationship to each other on coastal estuaries. For example the ebb current can run well into the rising tide.
Know your coastal speed over ground, it will usually be slower than calm water. Wind and coastal tidal currents will affect your speed. Have a plan for harbors of refuge on your route. Study the charts. Find those with local knowledge. Have good tidal and weather predictions for your route.
If you have no experience off the PNW coast start with Charlie's Charts U.S. Pacific Coast. Then dig in deeper with any good resources you can find for your intended route.
Probably the most important thing you can do beyond getting prepared and timing your crossing correctly is to have patience and flexibility. If you're headed out and you don't like the looks and feel of it before you get to the bar turn around and try again another day. If you're headed in and the bar is kicking up but you're uncomfortable out there, live with it till the bar settles down.