Tedd, a few things you have to keep in mind regarding going to a larger boat in the Vancouver area are the associated costs and difficulty of finding moorage. My CAL 2-25 (also know as CAL 25 mk II) is a cruising sailboat with 2,000 lb encapsulated keel, standing headroom, Yanmar diesel, cabin heat, head with holding tank, chart plotter, galley, tiller pilot, dodger, new sails, furling head sail, etc., basically all the systems and comforts one expects in an overall length of 26 feet. She is faster sailing and has more internal room, comfort than many 28 footers. She is setup of easy solo sailing. My annual moorage cost is about $4,500 at Thunderbird Marina in West Vancouver. The cost and difficulty of finding moorage, maintenance, upgrades, etc. goes up exponentially with length. Annual Moorage goes up by about $500 or more per foot and it is very difficult to find moorage for boats over 35 or 40 feet unless you go to Port Moody or the River. Put you name on marina wait lists now even if you need to pay to be on a wait list. You may be lucky to find a boat that comes with transferable moorage but they will be asking more money ($5,000 to $10,000). Moorage away from Vancouver such as on Vancouver Island is much easier to find and can be half the price but then there is the inconvenience of getting to your boat. You should be able to find an older fiberglass keel boat around 30 feet or less depending on condition $15,000 to $30,000 that will get you started. Plan on insurance (~$500/yr), survey (~$500) and maintenance costs of about $5,000 or more per year if you do the work yourself plus upgrades if you love your sailboat. By the way need $2,000,000 liability insurance to get into a marina (even for a day visit) and you can’t get insurance without a survey (and fixing everything that needs fixing). Do your home work first and happy sailing.