Licences:
Weapons: One per weapon category (or at least, the R-rated weapons) + one for concealed carry. (For categories, just look at the skills: pistol / automatic / rifle /...)
Bio/cyberware: One per restricted item.
Other items: One per job/cover/category. What makes a category? Let's say your SIN says you're a wildlife photographer. Then you might get away with putting chameleon gear (so the animals don't see you), shock frills (protection vs. predators), maybe even a laser microphone (find out if something's in that nest), grapple gun (to get to difficult places) and some gas (protection vs. predators) in a single license. You will have a hard time explaining why you need anti-technological or lockpicking items with the same license, though.
A drivers licence or stuff like that don't need to be bought, they're part of your (fake) SIN.
Group Contacts: Hmm... Good point. Would saying "9 maximum before applying the Group Modifiers" fix it? If not, I might just drop the restrictions... As posted earlier, it's already a 'soft' limit anyway. If you can come up with a reason why your character's got that kind of connection, the limit can be (re)moved.