SR 3rd edition: FAQin' hell some rules are dubious!

[comicshorse]

That's a lot of text !
I'm on my way out so I'll deal with the easiest point (for me)

Also, my mage guy bought one level of initiation, and his metamagic feat was masking... in line with the above query, wouldn't I now have to include awakened PLUS initiated casters in every single opposition group if I wanted to make sure he'd be singled out for "always geek the mage first" to actually be viable? Because, by the player's own admission, it would be a huge penis move if I allowed him to buy masking to now start popping initiates everywhere and invalidating it. On the other hand, if one of the reasons drain is super tame is because "always geek the mage first", then isn't masking a sort of complete immunity freepass?

Firstly as Lord Torath said Masking can be seen through by another Initiated Mage, its an opposed roll.
And yes while it would be unlikely for Initiate Mages to suddenly start popping up everywhere the fact this he's now an Initiate shows he ( and presumably the rest of the group) are moving up in the world. This means higher paying but harder jobs where the opposition will increase in proficiency. ( Just the fact he can Mask now makes entering other countries for international jobs easier as the Mage won't get noticed at customs).
So while it doesn't make sense for the street gangs to start having Initiate Mages as members the P.C.s sound like they've reached the point where they should now be operating on a higher level. Dealing with more dangerous and prepared opponents then ever ( but for more money !)
Also you don't need Mages to challenge Mages, grenades give street-samurai area effect blasts ( and gas is nasty if the Mage isn't prepared), Riggers can pack Drones with heavy weapons that can shred buildings ( and you can't stun bolt a Drone !). If you're feeling really nasty there's stuff like F.A.B. and the dual natured Ivy (can't remember what its called) to make Mage's life hell.