I have a O'Day 39 shoal draft boat. How do you feel about it compared to the Sun Fizz? I know the O'Day was built under license from Jeanneau. I have heard negatives about the O'Day and similar produced boats. I have a small boat dealership I plan to sell as soon as I have either my 39 ready or my old Soverel S-28. I really like the small boat since it has no complex systems or even an engine. Please give me your thoughts.
Also I am a CPA and could arrange to come back to the states to do tax work every year to generate enough money to keep me going. Please give me your thoughts.
I don't think I'm the best person to answer questions about the right boat to sail. There are many, many people more knowledgable than I. You'd be better served by posting to a few cruising bulletin boards, such as the Cruiser Log board (http://www.cruiserlog.com/forums/forum.asp?FORUM_ID=2
), and maybe CSBB and SSCA boards.
What I know about O'Day: Jim Hunt was President of O'Day until 1987. He is a good friend of our most avid sailing friend. We spent a lot of time talking with him about our Jeanneau and the O'Day 39/40 (Jim Hunt had an O'Day 40, "Whale and the Bird" - built on the Sun Fizz mold with modifications). He sailed Whale and the Bird
from Massachusetts to the Caribbean, then up to Bermuda and across the Atlantic to the Med where he cruised for several years before reversing his trip back to the States. He trusted his boat, and we trusted our Sun Fizz (clearly, considering how long and how far we took her).
As far as negatives, even our sailing friend thought the boat wasn't up to what we took her through. Yet at no time did we feel the boat could not handle what was thrown at her by wind, waves, current, and our own sometimes foolish mistakes. I think that every boat has its good and bad features, as well as its poorly maintained or possibly poorly built hulls. If you like the boat and it meets your needs, the best advice I can give you is to take her offshore nearby and see how you feel about her performance, when you still are close enough to home base that you can do something about any concerns you might have.
Two of the most avid proponents of simple, no-engine sailboats are Donald Street and Lin and Larry Pardey. Don Street put an engine in his boat 15 or 20 years ago, even though his cruising was primarily in the Caribbean where the winds rarely fail. The Pardeys have been known to get a tow into port in various places, so their lack of an engine doesn't necessarily mean that use of an engine has not occasionally been welcomed by them. We spent two days watching a fellow in his small engineless sailboat try to sail into our anchorage in Thailand. Finally, a few of the fellows went out in their dinghies to tow the guy in so he could make it in time for our big Christmas dinner feast.
There are plenty of times when having an engine is convenient, and a few times when it makes life safer. Granted, sometimes it's just saving you from your own stupid mistakes, but I don't know anyone who hasn't made at least two stupid mistakes in their life. And there are places that you cannot go without an engine. That some day that might be the only place you can go might be remote, but at least you keep your options open.
You need electricity - for lights, radio, etc. Solar panels or wind generator can do most of that in a simple setup, but sometimes the engine is the best/only way to charge your batteries. Another argument for comfort and convenience, I know, but if you choose to go cruising and live aboard permanently, life's little comforts can make the difference between a one-year cruise, or a semi-permanent lifestyle.
Lots of choices, lots of ways of looking at it. I don't like super complex and I don't need total comfort, but I like some.
As far as earning money, it seems as if you have an excellent possibility for topping up your cruising kitty. If you keep your lifestyle modest, it could very well be enough.