Lots more good advice! and an update
Thanks everyone for all the advice, I am making some progress, sort of.
First, I spent a week driving across Canada and am now in Vancouver, so I can more easily see actual boats for sale in person.
I'll be test driving a Ranger in a week or two, as soon as I sort out a place to live (that's a whole other big decision process).
One thing I have been doing is calling marinas all over to get on waiting lists and see if they have any slips available, plus costs etc. Not making much headway there...that could be a big deciding factor of where I end up, which is looking more like Nanaimo or North of there, despite the fact I have a family member with a condo I can rent in Victoria, which would be a nice situation. IF I could get a slip in that area.
I was really hoping I would get to see the Emma B which was for sale, but unfortunately for me it has sold. It was probably about perfect for my needs, although the potential maintenance issues scared me a little. I did talk to both the former owner and the broker, but I just couldn't pull the trigger without seeing the boat in person, and I didn't make it in time. I did get my second Vax though, which was a big reason for my delay getting out here.
One thing I will clarify, I can see myself doing a lot of cruising the first year, but I am really very interested in finding a waterfront lot to build a home on (I have done it before, I like the challenge).
So if I find that lot or fixer upper, I would be spending a lot more time on land, while you guys anchor in front of me and wave as I slave away.
That's just one more reason i was thinking a smaller boat might be more suitable. I won't be full time cruising forever. And reliability is key, as I will be using the boat as my transportation to get supplies (I mean groceries, tools etc., not barge loads of lumber).
So the saga continues, but I am learning a lot and have really narrowed my focus. Looking forward to seeing a testing out a few boats in person in the very near future.
I'll be sailing around the Gulf islands this weekend on a friend's old sailboat. I think it will convince me I need new, and bigger.