big vs. small
I think there have been some very good points raised. I would like to weigh in here with a slightly contrary answer, if you look at the title of this thread, big vs small I guess I have to ask how that is measured. I normally think that displacement more than length really governs seaworthiness, carrying capacity, cost of maintenance, ease of handling,rigging loads etc. If you talk about two boats of equal displacement (Probably in the range of 15,000 to 20,000 lbs displacement), one a 36 footer and one a 41 footer (both with proportionate waterline lengths), the longer boat will have equal or greater carrying capacity, all other things being equal have greater speed, motion comfort and stability, a similar cost of maintenance,and generally be easier to handle shorthanded especially in light air or in heavier conditions.
Living aboard, the longer boat of equal displacement will generally have more useable space and more room for storage low in the boat.