I started my boating with a Laser in 1970. Mail ordered along with the thickest wet suit I could find, then launched it in a river North of the 55th parallel, in middle canada, in the first week in May. Dodged the ice flows, and ,like a dummy, intentionally rolled it ! I didn't have gloves so in seconds my hands didn't work but I managed with my elbows. Still have that boat and it still works fine.
After a hiatus of movong to different countries and starting a family, I ended up with a 1/3 share in a catamaran?? on the Gulf of Bone in Indonesia. Made from 2 X 45ft.dugout canoes, and everything else from scrounged industrial scrap. Deck was gap planked so it drained well and the kids would sleep with an eye glued to a gap as we would normally anchor on top of a reef and hang a dive light under the boat for the aquarium show. I really learned about using minimum horsepower with this - the auxiliary was a 45 Evinrude but as a backup we had an 8hp Yamaha long shaft that would push the craft at about 4 knots FOREVER. Accomodations were sparse, consisting of a doghouse which covered 4 single mattresses as a sleep platform. This would accomodate two families or 12 drunks for the "Boy's weekends".
After a spell back in Canada, in 1987*my wife (and I blessed the fact that I could always remind her of this) suggested we pack it in and get a boat and "sail somewhere". With a very steep learning curve, starting essentially from zero base, we went to our local library and got every book we could find on sailing and cruising. Of particular benefit were the disaster and clusterf@#$ books, which we would each read and then discuss how we could have avoided that. If we didn't know - back to the library.
I managed to find a mail order Coastal and Celestial Navigation course, bought a sextant and an artificial horizon for practice, then off to the local hardware store, where they had a sale on 4X 8 utility trailers.
We reduced our possesions to what would fit in a chipboard box that I fitted to the trailer, sold or gave away everything else, pulled the 3 kids out of school, hooked up to the trusty K car, then drove down to Florida 'cos that's where the magazines said there were these boat things for sale.
Luck must sometimes favour the dumb, 'cos we lucked in to a dealer called Joe Doman, who helped me find a suitable boat (a Dufour Sortilege ketch) which had been sitting in a Fort Lauderdale canal , for a couple of years, and had been struck once by lightning. He then kept coming back to check on us in this do-it- yourself yard in Dania, and was always dropping of nautical items that had come loose from some of his boat deals.
From Florida we sailed to the Bahamas, then Cuba, Panama and points west, fetching up finally after a couple of years in central Indonesia.
Time to get gainful employment and try the kids back into formal schooling, so end of boat and take advantage of a job offer with flights paid back in Canada.
From there a couple of old sailboats* ( a Grampian 26 and a Douglas 32) in the North Channel of Lake Huron.
I then made the mistake of reading a Dick Buehler book and got hooked on the Diesel Duck. Retirement was a possibility, so I got in a backhoe and excavated a shipyard in the woods behind the house. Ordered the plans from Dick, took a welding course, and for one of the very few times in my life rethought a plan.
When we sat down and worked out the time* commitment and our knowledge base, it looked like 2 years of bullwork and at the end we'd likely have Northern Ontario's largest and ugliest flower planter.
Started snooping on all the trawler webs, realised that we are very comfortable with simplicity - found a very interesting trawler last year in Toronto, bought it from a great guy (Wallace Gouk -if you ever need a boat surveyor in the Great Lakes area) then the wife and I brought it up through the Trent Severn to beautifull Spragge.
Best resource I've found for the sail to stinkpot transition has been the Marine Diesel forum ($25 a year), as, not having sails scares the poop out of me, and that big old Perkins is a little intimidating. We're off to Lake Superieur as soon as it gets liquid so I'll reactivate an old 9.9 Yamaha so I can use the dinghy as a tug if anything go's wrong with Big Blue (I have a 2HP Honda which I've used to hip tow* my Douglas when it's old Farryman gives up the ghost but it may be too small for this 23000 lb. trawler)
Rambled on enough