Re: Sailing a Cutter
I have limited cutter sailing experience, a friend has one and I've sailed with him a few times.
Tacking his boat efficiently does require an extra hand to pull the genoa around the staysail stay. Otherwise you tack almost 180 degrees to get the wind to push it through, then come up and sheet in. Dropping the staysail doesn't help unless you also remove it's stay.
I get having a cutter to have more options of sail plan (from all sails flying scaled down to a trysail with small staysail). If you plan on motoring through once you get to Victoria and head north then the cutter won't be a downside. If you want to sail you'll likely find yourself tacking often (winds in the Gulf Islands and north typically run NW or SE, leaving narrow passages to tack in) and wishing for the simplicity of a sloop rig.
If I were going offshore I would personally buy a sloop rig and add a removable solent stay from which to fly smaller headsails in storm conditions. That makes tacking easier but gives you the sail plan flexibility of a cutter. I'd also want a fin keel for better performance to weather and reduced wetted area.
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