When I was young we had a fun tradition where each kid would pick out a pumpkin, of any size, as long as you could carry it back to the car.
Naturally, we tried to pick out the biggest one possible!
But, I also remember taking extreme care with my limited and precious choice as I would need a decently-sized surface for carving and one that generally presented well — you know, overall curbside appeal type of thing.
This meant that going for the largest was not always the best decision and making small compromises on size for the sake of a better surface was, naturally, at stake.
A bonus was, of course, to be able to pick / choose smaller pumpkins and gourds that would accompany the larger piece to fill out the presentation or for siblings that couldn’t quite manage to pick their own yet.
Those were good times.