Anyone living on a sailboat wish they would have gotten a bigger boat? Or a smaller one?

Anyone living on a sailboat wish they would have gotten a bigger boat? Or a smaller one? I’ve only just begun my sailing journey and am a member of a sail club on an inland lake for now. I’ll probably start the purchase process for a livaboard in the Carribean this coming year. I’m very picky and would like to know how does one get aboard lots of boats to look around and get a feel for them? Thanks

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