I think you have a pretty solid plan.
Like many other folks we started a similar journey. the
boat show">Annapolis
boat show is a great place to see what the market is currently offering. Sail on as many
boats as you can to see what you like and don't like.
Classes, charters, friends are all pretty
cheap ways to see what works and what doesn't. Also a good way to see if a Cat offers what you are looking for.
For years we sailed full time on a friends Freedom 32 coastal cruising, best sailing value I have ever had.
Our first boat was a
Hunter 336, our 2nd was a
Hunter 410. Production costal cruisers give you a lot of amenities for your buck. The hunter 410 was a great boat to sail and pretty comfortable. It didn't have a
generator or a
water maker but plenty of
water and house
batteries to keep things going. It also had A/C so when you get to many rainy foggy days pull into a
dock and turn On the AC. While both
boats were great, they were not the boat we would take for extended
offshore cruising. ( although, many have done exactly that)
I wouldn't start outfitting the boat with world cruising
gear till ya ready to go and know you have the right boat. For example our
current boat we don't have a
water maker. However as we increase our
offshore trips and
remote locations we know we will add one. But for the sailing we currently do it is not required and probably won't be used very often, and would be another system to maintain. Then we we do go on extended trips we would be starting with a ten year old
water maker.
As we have grown in experience our boats have also grown. This past summer we competed in the Marion
Bermuda race, I believe there is a similar
Annapolis to
Bermuda. While we can debate if the US sailing rules are overkill, I did appreciate the structured approach to looking at mechanical, and
safety gear, including storm
sails and heavy
weather sails. For us we used the
race to get the boat ready for
blue water sailing. We spent the good part of the year before getting the boat ready for the race. After completing the race and returning I feel the boat and us our another step better prepared for larger journeys.
Good luck and enjoy the adventure