@kitteh I've always had a similar problem--I decide to "play it safe" and stay under the chargen max (whatever the Staff has decided that to be) because I don't want to be too twinky, and then my "specialist" is objectively worse (not a whole lot worse, given that it's usually 1-2 dice, but still worse) than other specialists because I didn't min-max at the game's start. And because of the linear costs in Chargen and accelerating costs with XP, it's very difficult to catch up. It still happens to me, and I've started just telling myself "it's just one or two dice, it's not the end of the world," which helps a little and is true, but there's often just that little annoyance still there.
One more thing that I really, really like about FS3 that helps with this is that sheets are visible by default, so you can always look at the sheets of those who are already doing the role that you're looking at, and see what level their skills are at. Of course, this doesn't help if you're one of the first to chargen, but if you join in later it's nice.