Wow! I am blown away by all the responses in less than 24 hours. Thank you everyone for the info, advice and warnings. The first thing to say is that the person I am going with is more knowledgeable about sailboats than myself. I am trying to read, explore and learn as much as I can about various types of boats before we start looking at specific ones so that I can help with the boat search rather than tag along and watch..
As for sailing experience: Both myself and this friend owned a Cal 20 for a year and did numerous sailing trips on board it. We spent 5 days on it once, sleeping in it every night! (As I'm sure you all know the cabin in a Cal 20 is tiny and there no amenities). So our comfort is not really our first priority because we will be able to outfit whatever we have to be more than comfortable enough. My friend has also crewed on many boats in the past including multi-day races, races around Vancouver Island, etc. As I said, thanks for all the warnings and tips on things to look out for. These are all things that I understand my friend is experienced enough to look after, but I want to have a good grasp on how to inspect a boat and what to look for and how to outfit it to make it safe for our trip.
It seems the consensus is fairly mixed as to whether we are insane fools, or just slightly crazy adventurers! I would hope it is more the second, but I will continually re-evaluate the situation as we keep planning and if it seems too stupid then I will look more into the crewing possibility.