Not sure if I have much to offer but I did
anchor in Vancouver once for 4 days in summer of 2019. I tried to
anchor in false creek but it was packed with dodgy looking boats too close together so I dropped the hook further out near Kits Beach. Kits was really rolly and unpleasant despite low winds. Lots of wakes rocking the boat all the time.
I have a 26'
sloop which is relatively inexpensive compared to most boats but when something needs replacing it costs big bucks. The bigger the boat the more expensive everything is and the more trouble you can get in. You'll also have a harder time finding
dock space for the inevitable marina visits. I heard Shelter Island allows live aboards but read mixed
reviews on the experience. It sounds like things have gone downhill there in the last few years.
From personal experience trying to
work from a newly purchased old boat you're going to have to contend with unpleasant things like waking up to do anchor watch at 3 am when things kick up. Even if you have a great anchor the odds are your neighbors do not and you have to be ready to deal with people dragging anchor into you.
You can get by with
solar panels but a big boat whose owner is on his laptops all day is going to require a lot of juice and when it's cloudy ( like most of the winter) the
panels provide little energy. Personally, I'm thinking I will
cruise in summer and spend winter at a dock working while attached to
shore power, it's just easier.
Best
advice I'll give anyone with little or no sailing experience is do not rush into it.
Buying a boat is like getting married, you need to choose wisely to keep your bank accounts from bleeding dry.
Maybe try to spend some time aboard some boats first. In Vancouver, I'm sure you can get aboard one of the many barely used boats and see if you like it. You might need to bribe them with a few bucks but it's nothing compared to
buying the wrong boat.
I'd offer to take you out for a sail but I'm away at
work and my boat is ashore.
Trente Pieds was right, there are a ton of sunk costs in boat
ownership. If you want to do it for the love of
boating then great but I don't think the possibility of saving a few dollars on a cheap boat is worth the many discomforts. Perhaps moving to a cheaper place outside of Vancouver is best. Port Hardy is reasonably priced.
Anyway, looking forward to seeing what you decide.