I really guess it depends on how the org feels. My boyfriend is part of a local fraternity with only one chapter; if I wore his letters sweatshirt because I was cold, and he lent it to me, they most certainly would not care. I know all the brothers quite well, despite the fact that they go to a different school several hours away, and we're good friends. If they cared, however, I would definately not want to wear his letters for any reason.
Since they are local, a lot of their rules and regs are much less strict than national GLO's, though, which may explain the fact that they're a lot more lenient. They encourage letter wearing because it gets their letters out there more.
As far as little sisters go, I was told that the REAL reason why it was discontinued is because there began a habit of the big brothers expecting sex from their little sisters - that it was a tradition, and pretty widespread. It sucks that it's not allowed anymore, though, because it would be pretty cool.
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