In 2003 I bought a 1974 27' O'Day and lived on it for 5 years, (it's for sale in Pensacola $4,500) in the last year of live-aboard I picked up a female yellow lab from the Humaine Society; we are still best of friends - she was 6 months old when I got her.
The only problems I had were leaving her alone on the boat, she became bored and chewed a few things including one of the planks in the companion way and all the wires to my PC... She was also a little nervous on boarding the boat - now she's willing to board almost anyones boat! She loved the boat and sailed with me a lot - it was "her boat". In fall 07 my soon-to-be wife and I bought a 48 ocean going cutter ketch - A Soverel 48 - we married in January 08 and I moved ashore while we prepare the new boat for circumnavigation.
When I bought the O'Day I had only sailed 2-3 times in my life and it had been a good 20 years since the last time. I had just finished a year long motorcycle trip from Key West to Anchorage to Washington DC to L.A on a 1979 Harley Davidson (some 34,000 miles in a years time www.bruce.milne.com
) and I was not keen on returning to a normal life so I begain looking at all the different types of vessels - I bought the O'Day for $6,000. It has 6' of head room and she sails great! I'm in Florida so I needed A/C, I installed a 12,000 BTU window unit in the old engine compartment and routed the heat exhaust out a cockpit locker via 12" duct work.
I learned to sail by first walking marinas day after day and figuring out what each rope and object on the boat did - I had done this for several months prior to buying the O'Day. I went out and motored around for a couple of trips, then I raised the main - not much happened - so I raised the 150% Genoa- whooo-eee, we be sailing and I have been ever since. There was a lot of terminology I didn't understand and sailing books assumed I knew all the terms - I did not - so I bought sailing for dummies and went sailing, when I ran accross something I didn't understand I looked it up in Sailing for Dummies - quite easy to understand. After a while I looked into other books but Sailing for dummies answered all my questions quite well.
The first real maintenance I did was a bottom job in January 04, I would not drill a hole or do anything unless I was sure of what I was doing and took the time to do it right. For the past year my wife and I have been preparing our 48 Soverel for circumnavigation - we bought it from a charity and needed extensive hull work and an engine plus many other upgrades; it will be another 6 months before we're done - I have gone slow and I have made mistakes but we are gettin it done. Self taught is the best way to learn, this forum should be very helpfull in your journey.
I say - jump in, enjoy the boat and sail away; life is short and we can't take possessions with us... Maybe we can take our dreams and our memories with us and on the chance we can, I'm trying to make as many great memories as I can. I made the memories decision after a cancer scare in 1997, a thing like that will change your perspective on what you value and on how you lead your life.
Good luck - Bruce & Lisa
Buy your boat, keep your dog, welcome to the sailing life! Dogs are like humans in the way they acclimate to thier living conditions.