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In my experience most people that have low social skills or are shy turn to chars that only need low social skill (or are shy) so actually they play that role quite well, but if they want to try something else, they should do that and they have the best chance in succeding if they can use the skills their character has instead of being limited to what they themselves can accomplish.
Now, this is personal bias, but all the players I have yet seen who resort to this have been, well ... let's say unpleasant personalities. Shy players who may not get around to smarttalking can be taught, self-righteous dice lawyers and/or people playing to gain spotlight and demand attention or "win" at dice rolls, however, cannot. Usually, the latter cannot take criticism of any kind, either, so attempts to better them won't necessaily lead anywhere.
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Likewise if i have someone with no medical experience playing a medic i give him hints regarding things that his character should know (if i know them) and if he is telling wrong things for first aid, it is still that test that counts.
To some degree, yes. I expect people to know the fluff ansd crunch respective to their roles too, at the very least when they have been playing for some time. Knew this one player who hung at my group and did not manage to buy herself a BBB in 4 years, because she could always beg for someone to explain the rules to he, over and over and over and over again. And they say SR4 is so simple every idiot can understand it. Well, no, and that's proven.
I do not expect players of a medic to know medicine. If they do some research and, say, steal phrases fom ER or House or whereever, fine, I'm grateful and may reward this with RP Karma occasionally, but it is not mandatory. However, I expect theem to know the surgery rules, and what medical options there are in SR, rules for medkits and their rating, biotech tests, synthskin ect. Same with other characters. If the player branches out beyond the rules/game background stuff, that's great, but not demanded.