Bigger...
Its too big when you cant get the anchor up by hand after the windlass takes a dive
Oh but you can sail that sucker out or use the engine, right?But seriously, in going from a 23 to a 33 the biggest advantage was that the larger boat can get out of her own way under sail. Small boats just wont hack it when going to weather in even moderate (20 k) conditions unless its an all out racer. Sure, it will go to weather in flat water, or for a few hours of thrill sailing, but a loooooong slog upwind to get somewhere is not all that thrilling. In my 33 foot boat, that looooooog slog is merely loong. its do-able. the 33 fotter will pull a half full dinghy like its not even back there. So far as space goes, It allows one to collect a lot more un-needed junk. I live by myself on the boat. Its a total waste of space for me. I was quite comfy on the 23 foot cutter.So I guess mu answer is that the length and therefor sailing abilities, might make the larger boat a better deal depending on where you sail. I still do like small boats because I tend to sail them more. Also for folks on a budget, replacing items on a smaller boat is a lot easier. Compare stay-loks for 3/16 wire VS 3/8 wire.
Its too big when you cant get the anchor up by hand after the windlass takes a dive