Hi there,
I live in Victoria on my Westsail 32. It is my first boat, and I learned to sail on it.I have been living aboard for 5 years and I highly recommend it. I have yet to travel the world and my sailing skill set would be considered beginner to medium, but I learn something new every time I am on the water.
If you want to drop in sometime and check out the boat, just drop me a line. Give me enough notice and we can go for a sail sometime. I am moored in the Inner Harbour at West Bay.
There was a quote in an Eric Hiscock book that I'll paraphrase - it said something along the lines of "men of a certain age that want to learn to sail should do it on a full-sized vessel with all of comforts of home, as opposed to getting cold and wet splashing around in a dinghy which will scare people away".
If you decide to buy a succession of smaller to bigger boats until you get to one you can travel the world in or liveaboard comfortably you'll find you should've gone straight to the right boat the first time.
Also, once you start doing your research you'll find out there is no such thing (that I am aware of) as an inflatable sailing dinghy. Or at least not a serious one. There is usually a difference between a sailing dingy and a tender for a cruising boat. There is some crossover, but a sailing dinghy needs a keel (and sails), a rowing dinghy doesn't.
Try to find a copy of "Desirable and Undesirable Characteristics of the Offshore Yachts", there are lots of used ones on Amazon. You'll find the Westsail fits the bill for everything - heavy displacement, full keel, cutter rig, small cockpit, small sturdy portlights, heavy duty construction, etc., etc., etc.
My advise would be to try and save a year or so for a down payment to lessen the amount of time you have to finance. It'll put you in a better position to arrange that financing as well. If you have the ka-ching to put down 40% or more on the boat it makes it easier to get the boat you want. Try to get at least 20%. Remember to calculate in taxes, lawyer fees, transportation costs etc. If the boat you get has an original or old engine, budget about $12G to repower soon. Same goes for all of the systems - plumbing, electrical, standing rigging, sails, etc. If it's old, it may be time to be replaced.
Don't buy the first boat you see - check out several, and check the forum to see if any one else has seen the same boat before you go look - they may be able to save you a trip.
Decide if you are project orientated and are willing to spend the time and energy to take on a project boat or are willing to spend more to buy a boat in better condition that needs less work. Time and energy and skills I might add.
Some other pundit on the web suggested that a good way to see if you are even compatible to boat life is to move into your garage for a month or two and see how you can handle it. However if you are already in a VW van in Ukie, the W32 would seem cavernous.
Good luck,
Stephen