mast/sail compatibility

topic on its own
picking the right sail for the conditions

my buddy says "bring all your stuff to the beach"
then change out sails n boards as required
he spends more time pickin n choosin than i
i am usually on the water within 20 minutes
for him double that
and he will change out more than i
i think i will be satisfied more easily than he
even if i am not planing, i can have FUN
if i am OP/overpowered - no issue - tighten it up and learn survivor mode
TOW = FUN