OK, pretend elf argument commencing.
I think a better lens to view things through is the idea of stackability. That is, if two people have the same ability (possibly at different levels), is that better than if just the better one had it (by an amount significant enough to matter)? If no, it's not a stackable ability. If yes, it is. I would argue that everyone should try to pick up stackable abilities IF they have low enough opportunity costs to be worth it, but nonstackable abilities should stick with the specialists. Drones can be either because they are a large category. Let me give some examples.
Hacking is nonstackable. Only the best hacker really matters, because teamworking hacking checks greatly increases your odds of getting caught since the target gets twice as many chances to see someone; even two equally-skilled hackers are best off having only one of them hack any given system. Now, a second hacker might be handy so you don't have a single person doing all the hacking (in case they go down when you desperately need some hacking), but it's certainly not worth having your entire team be good at hacking - you really get nothing out of it.
(You might also benefit from having two very different hackers, like a technomancer with a heavy focus on stealth and a hacker with a lot of the "utility" programs, so the techo takes care of hacking big scary nodes and the hacker handles all the stuff like editing footage or decrypting files that the technomancer couldn't afford to be good at, but this is more a case of subdividing a task than stacking it).
Shooting people is stackable. Anytime you need someone shot, having more people shooting at them helps. A samurai with 20 dice to shoot people does not do the job as well as a samurai with 20 dice to shoot people and 4 other runners with 10 dice to shoot people.
Drones, like I said, can be either. You don't need two people doing drone scouting - you want the best rigger doing it since they are less likely to be caught. You might, however, want an autonomous drone to back you up during a fight, whether or not you are a rigger - since if the rigger ALSO has one, it stacks. Similarly, it might be worth having your own transportation, because you don't always want your entire team going everywhere together.
