One of the things that happened with me, as far back as SR1, was a disconnect between what the game seemed to say was possible, and what was actually possible. I saw no reason, as a GM, not to have cameras inside elevators, recording who used them, or motion detectors inside vents (mostly for dealing with vermin), and as my knowledge of technology (and the world's ability to use technology) advanced, I started seeing things like facial recognition software and the like.
So a part of me, early on, went, "How the hell do Shadowrunners keep anonymous?" and the answer was, "With a lot of work."
It's one reason I made Koryo. This was a character who believed that being spotted was the greatest sin. That having anyone notice you on a run was tantamount to failure, regardless of the outcome of the run itself. I bent over backwards to get the proper contacts, spells, and techniques so that he/she could ghost through a run without anyone noticing him/her. It is hard work, but when the run goes off without a hitch, I feel a special sense of pride.
I had to hit that special balance for running the game though - tailor the adventures and runs to the PC's skillsets. The PCs don't tend to do 'stealth runs', because they have no means to deal with the requirements of a proper 'stealth run'. Funny enough, the most recent run required kidnapping a rockstar, and to do that, they did the following:
1) Get a car that looks like the one the limo agency uses.
2) Get a second car and have it cause a traffic jam in front of the limo heading to the target.
2a) Have the technomancer block the 'call' going out from the jammed limo, indicating there will be a delay. Send a reply to the limo that says the call has been received.
3) Drive the fake limo up to the entrance, and get the target in.
3a) Stun bolt the bodyguard, and drive off, saying that the bodyguard is being attacked, and the target is being brought to a safe house.
3b) Really make those diplomacy rolls.
4) Copy the signature of the proper limo to that of the fake limo, for when being chased by security.
4a) Swap signature with actual limo, and 'vanish'.
5) Jam car departs, and security shows up at actual limo.
It went... reasonably well, actually. The players put a lot of work into this, and they got all their rolls off.

I thought it was a well-thought out heist job.