If it's just the hole that the pin goes in, I don't think there should be an issue. It is not recommended that you sail with that pin in place, anyway. If the mast falls down while sailing (for some strange reason like a parted shroud or something), you don't want that pin causing more damage.

Under normal (and some not-normal) sailing conditions, the shrouds and forestay keep the mast in place if they are tensioned properly. Even after you flip, there is sufficient tension to keep that mast situated properly on the mast ball. I've never seen it come off unless something catastrophic happened first (shroud pin breaking, damage to main beam, etc)

If you're comfortable raising and lowering the mast without the pin (not recommended, but possible) I see no need to spend a lot of time worrying about it. The pin is supposed to keep the mast from slipping off that ball while you're raising/lowing it.

while you're on the topic, couple of things to check each time you're going to sail:

- all pins checked, secured with ringding and preferably taped in place. This includes shroud, forestay, bridle wire, and spin bridle pins)

- shackle at mast hounds (where shrouds and forestay meet at top of mast) is properly fastned so it won't unscrew and part while sailing (yes, it's happened)

- check the hounds where all the wires meet - sometimes that hole stretches out and develops a crack which might eventually fail

- shroud chainplates need inspection to see if they might let go. I don't know of any that have (for something other than the pin falling out)