Originally Posted by tommays
From owning a 29' boat and regularly racing on many others every time I step on say a J44 it is just FREAKING BIG and every aspect of big makes everything a much more physical task
A simple thing like taking off the sails before winter storage NOW requires a small army of friends as the 44' boats mainsail is both big and heavy
Your certainly looking at a size were things like electric winches and all the complexity that go with it become almost mandatory
The 29' was very much chosen on the workload I feel comfortable with in both repairs and sailing
Well at age 65 I single hand a 44 footer up and down the islands out here in the Eastern Caribbean and while I do have an electric anchor winch all sailing winches are manual and I have no problems.
I have a full batten mainsail made from heavy weight dacron and yes it is a pain to handle with the battens in. So I take them out.
I would not see 40 to 45 ft as being too large for you to learn on with one important caveat which is berthing in tight marinas. Any larger boat can not be 'muscled' around so you will need to learn the 'tricks of the trade' when using lines and cleats to slow stop or turn your boat. Also some dinks are to be expected. If you face a situation where you will be berthing in confined spaces often then a bow thruster is a good investment. They can be retrofitted to most boats.