I hadn't seen this post before or I would have jumped in sooner. Sounds like Faster has you on the straight and narrow path with some good advice, he is likely the most seasoned Sailnet member in the PNW.
I have only been sailing since 2003 and started crossing the strait in 2004. I sail out of Point Roberts because I live in South Delta so I am out in the Georgia Strait regularly. It can be very calm, in fact I am sure I could paddle my canoe across it on some occassions. I regularly go for a quick dinghy spin when I am down at the marina just to see what it is like out there and I swear I could run my 9'9 dinghy with it's 5HP engine across no problem. But, I would never chance it though, I have been caught too many times by an unsuspecting strong breeze that comes up out of nowhere un-anounced.
I sail a 26' MacGregor and my wife and I cross over to Active Pass every summer. We have encountered some pretty serious wind and waves out there, the kind that keep your knuckles white while holding the helm. I have come out of Active Pass heading home to PR
to flat calm water thinking it is going to be a long slow run to the marina only to get half way across and fiind myself in a small craft warning with the rails buried in the water. It can be very unpredictable at times and when the winds do blow they can blow for days keeping you from heading out in your small boat. We were caught up in Snug Cove, Bowen Island last summer at the beginning of a blow that lasted days. I convinced my wife we should make a run for it down the coast to PR
while it was only blowing 20-25 knots because I knew if we didn't we would be there for several days. It was a 5 hour rough wild ride and I would not do it again, it gets pretty bad out there. (At least it was clear and sunny)
In my opinion the choices you are looking at are more for messing about in English Bay and having some fun and learning to sail. If Desolation Sound and the Gulf or San Juans are in your plans, look at a bigger more comfortable boat. We are cramped in a 26' MacGregor but it can and does get us all through the San Juans and Gulf Islands but we stay at marinas for the added creature comforts and conveniences.
The big advantage to trailerable is that you can travel at 60mph to some of your destinations or at least get much closer to them at the outset. Personally I would tow my MacGregor up to Lund then set sail to Desolation from there or tow to Port Hardy and sail to the Broughtons, it is too far to sail from Point Roberts all the way up there, even though many others do it I prefer not to. I would not even remotely contemplate it in the smaller boats you speak of. The boat gets real small real fast when you are out there for a few days and standing cabin room is almost mandatory.
You have some aggressive aspirations and I am sure over time you will realize your goals and acheive them but for now learn to walk before you run and try taking baby steps. A Canadian Power Squadron Course is highly recommended and then a few short overnight practice cruises.
Many folks moor over on the island side just to avoid some of the surprises the strait can dish out, it is much easier to sail between the big island and smaller Gulf islands than out in the strait in a small boat, you will soon discover this. Good luck in your search and keep in mind they are called daysailers for a reason.