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Either get a trailerable or secure a mooring slip before you buy the bigger boat.
And while shopping for a slip in the greater Vancouver area try and get a feel for where you would like to sail to avoid having to sail where you moor. Think about how far you may have to motor before you can put your sails up or how far you have to travel before reaching the Georgia Strait. English Bay will suffice for learning but it won't be long before the Gulf Islands bekon you. It is a long haul out there if you moor down the Fraser River and Sandheads can be very intimidating at the best of times, best avoid the river entirely. Mosquito Creek and other Marinas around Howe Sound will give you close proximity to the Strait and Islands or the Sunshine Coast. Marinas in False Creek open up English Bay to you but there is no longer a gas station at Burrard so you will be hooped for fuel. Going up towards Indian Arm only makes future trips more onerous, so, not only are you limited by availability, but also location can be limiting.
Where do you live and how far are you willing to drive to the boat and how much hassle are you willing to endure? This will have a big impact on how much enjoyment you will get from your new boat. Do you prefer to drive the car further for good sailing or would you rather drive a short distance and always motorsail out to where you can really spread your sails.
My first boat was and still is 26' and I slip at Point Roberts, just down the road from downtown Tswwassen. I have a Nexus Card for my constant border crossing and I live in Ladner so the drive is only 15 minutes. Customs is a hassle but a neccessary evil. In exchange I have one of the more favourable locations in the greater Vancouver mooring scene. Within 5 minutes of leaving the marina I am right out there in the Georgia Strait enjoying the big surf and within close proximity of the San Juan & Gulf Islands. Location is a big concern for a sailor new or seasoned, get the slip first and boat second, that will help you decide how big the boat will be because it has to be within a couple feet of the slip length. Good luck getting a slip over 30' , you'll need it. You may still get one at Point Roberts this fall when the seasonal transients vacate them.
A bigger boat can be more of a want than a need for a beginner, consider what the bulk of your sailing will be, day sailing will be the mainstay until you learn enough to leave the pond and that may take a while depending on the available time you have to invest. Even with my close proximity to the marina and the open Georgia strait I still mostly daysail and only do the extended week long trips in the summer (July).
Also consider your return on investment, you know full well as I do how much it rains here, just because this summer we got spoilled does not mean it will be like this next year. The last two summers before really sucked and surely you remember how long cold and dreary the last couple winters were! It is a lot of financial eggs in one basket for a bigger boat whereas the smaller boat is fewer eggs invested for the return on investment, never lose sight of our short sailing season. And yes we do get longer ones, I have had a six month one but they are rare. A 26-32' boat will do just fine for your first 5 years and maybe then some. How often will you single hand? A smaller boat is easier to single hand and dock with. Most of your time will be spent in the cockpit during your learning curve so big room below will not be a huge issue. Heck, you might even not enjoy the sport or afford it after a few years and want out, so keep that in mind. Leave the extra 3 feet off until you have a better idea of your needs.
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