Driving is not pain in the ass to raise, as soon as you've got some money and some time you can easily afford a few weeks of drivers' ed at the university, giving you enough skill to get started with (or more if you like). Security, on the other hand, can't be trained at the University (AFAIK), can't be trained from scratch at all unless you've got a liberal to teach it, is bloody important and isn't routinely found on any easy-to-recruit NPC. In a recent game I desperately needed security for my computer expert who had just been released from jail - she had to bust my founder out as well. Well, it took quite a while (in real time, in game time it was just a few days because I've turned table despawning off in my copy for experimentation) but I found a single teenager with security skill 2 - I had my hacker be teached to level 1, and after that she grinded stealth by stealing cars (lots of them) and robbing the housing project.
So, I'd like if there was an obvious security NPC for hire (like there's one for almost every other skill), or some other means to train the skill from scratch. Looking at the source, the only creatures that are meant to get security apart from random skills are mercs (tough to recruit), hardened veterans (need I say?), about 1 prisoner in 10 (easy to recruit but the odds aren't good - and since you probably release them, you'll have plenty of unwanted people to get rid off) and thieves (appears as some less-suspicious creature, so it's trial and error more trial).
SUGGESTION: Would it be good if street sense enabled the squad to see through character disguises? Or perhaps even CCS membership at a glance?