Welcome to the Vancouver Island area. With the right boat (meaning mostly the needed equipment), you can boat all year round here if you desire to do so.
I agree with all of the others who say the best cruising is north of Nanaimo, although the Gulf Islands in the off season are great as well.
Speaking from personal preferences and experience, if doing extended cruising (meaning greater distances and/or longer seasons) I would want a larger boat than a Ranger 27. There are many well built boats like Nordic Tug 32/34 or American Tug 34 that would make great boats for single handing (especially if equipped with both bow and stern thrusters) as easy as possible. They would be reliable and comfortable in most weather conditions around here. Obviously for comfort, a person would "pick their travel days" when crossing the Salish Sea and some other areas. Those boats could also be used as "live aboards" for a "minimalist".
In these parts, live aboard moorage can be hard to find. Most marinas either don't allow it or set strict limits and in those cases vacancies are rare.
As an aside, if you are not willing or able to do any of the necessary boat maintenance yourself, it will quickly become very expensive. Labour rates are over $100 per hour. Plus, when you are on extended cruises, it is best to have some idea on how to deal with "smaller" repair and troubleshooting issues, as at times help can be hard to find.
Good luck on your dreams.