Sup Pete?
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Honestly it really depends on the skill in question. Some skills have much more support and opportunities for larger pools than others.
The Social Skills are very much supported in this way. For example, not only do you have a slew of implants, adept abilities, spells, and gadgets that increase your pools, but also you have many situational modifiers that can be used. I don't have the book in front of me, but there's a chart that takes up a whole page and is nothing but modifiers for various Social skill pools. Even somebody with a lowish Charisma and little to no ranks in a given social skill can beef up his tests nicely. A Charisma 2 troll, using that chart, can still be very effectively intimidating if he plays the right angles.
There's even some decent support for most Combat skills. Everyone knows about how to ramp up Agility and Skills with the right implants and powers, specializations, smartlinks, etc. It's quite possible to get pools easily into the 20's. The 30's might be pushing it.
And then you have some skills with almost no book support, like Diving or Parachuting. Check out those skills and see if you can find a chart somewhere with modifiers in it.
Again, it depends largely on the skill. One skill might be hard to raise up to 14, while another is almost effortlessly taken into the 20's or 30's with all the options in all the books taken together.
But you also have to keep in mind that if you're pushing a skill into the 30's range you are doing so at a serious detriment to other things. I've found that the higher you want a certain pool to be, the more you must invest in terms of your resources to get there. So yeah you might be Annie Oakley with that rifle or you might be able to convince the local chapter of Humanis to throw off their robes and take ork wives, but you are going to be short in other areas that might round you out and make you useful to the team more often, rather than just being a tool for a single job.
Example: When I was using Bane in your game, I had Magic 5, Spellcasting 5, spec. in Manipulation spells, +2 to Manipulation spells from my Mentor Spirit, and a Force 2 Power Focus. Those are "only" 16 dice for casting Manipulation spells. And I put alot into getting my pool that high, such that he wasn't much of anything aside from a magician. But he was a powerful magician, and you can attest to that. He helped the party out good a bunch of times.
The best way to challenge a character with a high pool is to put them up against a situation where that pool won't help them. Of course that's where the REST of the team comes in...