Well, people don't "level up" IRL. How far you can see depends on atmospheric conditions and the binoculars you're using, not how much time you spend looking out over the sea.
Imho it's annoying to point the DG at a target, but see the shell flying the wrong way because you're skill is too low. Or hearing a ship on the hydrophones but not being able to report it because your skill doesn't allow you to pick up targets at that distance.
Imho leave the skill-points/leveling for the NPCs to reflect their gain in experience, and just let the players skills reflect the kaleuns capabilities.