Random thoughts: (apologies if they're obvious)
If you're doing a bit of extended cruising, you'll be able to watch the forecast and cross when opportune. There are cool hangouts to either side if you're waiting for weather, and it's a fine sail in good conditions. Ugly stuff usually gives you a break after 48 hrs or so. I try to set this expectation with all aboard so that they don't see postponing for a day as some kind of failure. Hudson Pt Marina is my favorite in WA.
Current tables are vital. Watch the wind-against-current scenario -- Especially if the current will hit max when you're mid-channel. If you do Deception Pass, go through at slack transitioning to pushing you onward.
Have a "Plan B" that's downwind. Nearly everywhere in the northwest, you can 'turn and run' and be snug somewhere in a couple hours. Have the charts and cruising guides for alternative ports of refuge.
Consider your crew. If they're not used to heavy seas, factor that into the go-no-go decision. Also, I encourage people to take pills or put on a patch before setting out. I can't tell anyone what to do, but over and over I see people doing the no-no-no-I'll-tough-it-out thing and being miserable instead of taking appropriate medication and being healthy through the passage.
This goes without saying, but study the harbor entrances, especially if you're coming in after dark. Victoria is well marked, but there are nasty rocks outside the channel markers. I'm amazed at how many people smack something hard in these areas, and I think it's mostly being a touch fatigued and focused on tasks like lines/fenders, customs and dinner reservations rather than navigation.
My best luck spotting Orcas has been between Cattle Pt and Pt Partridge.
PT to Victoria in a southerly with favorable current is a great ride. Beating into a strong westerly that's fighting with an ebb current can be quite ugly. Here's wishing you a southerly on the way up and a northerly home!
Be sure to consider your plan for clearing customs/immigration on the way home. (Locations, phone numbers, office hours, etc.)