Anchoring full time in Vancouver is a bit problematic these days too (Sorry to rain on your parade again) False Creek, which offers best shelter and convenience, is restricted to 2 weeks every so many months, and requires a permit. This has forced such people out into English Bay, where every year a few of them wash ashore in storms due to inadequate ground tackle, heavy wind and big waves. Last night would have been a sleepless one for you too. (or you may have woken up half way to Nanaimo)
There are several people doing it, and technically it's legal except overstaying your permit in FC or trying it on in Vancouver Harbour, but it means long periods with your boat unattended (while you're at work) and you're at the mercy of the weather. Also getting water, pumpouts, charging batteries etc are all going to cost since you'll likely have to take transient moorage for some of those tasks - but as you say, much less than full time moorage. Another issue is where to leave your kayak/tender during your shore time.
btw, glad you're listening to reason re: the 47 footer.. I do like your new focus better and your selection choice is now wide open. But you may find it's not as simple as it sounds. Good luck.
At least im progressing towards less ignorance. I found the question and answer section and read as far back as it goes until 5 am today too, that had lots of things to consider too. Dimple and easy are not required. Possible is definitely a good idea though. You are not raining on anything, I really appreciate the info and patience.
everyone who has replied taught me something, or gave me a new area to add to my list of topics to research.
Time and stubbornness I have, money is much more finite. I need a challenge, but want to manage the risks as much as possible. I'm going to start a new thread on it to explore my options since this is way off topic now, I'd really appreciate the continued good council if you don't mind the total beginners questions I have.