Originally Posted by pwillems
On that basis, are there any valid arguments to stick to something smaller and simpler?
Well, my C22 can be quickly trailered to unique sailing destinations with a comfortable Volvo station wagon, it's easier to sail, and needs less maintenance. If money was no object I might (or might not) get a bigger boat or better equipment, but I doubt I'd have more fun as a result.
Someday I might want a bigger boat if I have time to do a long bluewater trip, if I have the option to live-aboard, or if I had kids and needed more room.