Something that's been on my mind lately is whether or not to pop whiteheads. Is washing your hands, cleaning the area, popping a small pimple, and then applying benzoyl peroxide spot treatment, really the worst thing you could be doing to your face? Although the area might become a little more red, the pimple certainly shrinks and doesn't turn into a monstrous looking cyst. What are your guys's experiences with popping versus not popping?
It always depends on the pimple. Some may have a whitehead, but there could be crud beneath that that you just can't get out, and then you're tempted to try anyways and you just end up making look 10x worse. I always refrain until I'm certain all the junk is at the top until I pop it 
I think it depends on the individual and how the pimple looks. 
I used to be totally evil to my face and try and pop everything, it was awful. It made things much worse because I'd get more zits in that area and I'd wound myself badly, even tearing off the scabs afterwards so that I could cover it with makeup. What was I thinking. xD
Over the years I've gotten slowly better, and now I only rarely pop something. Like carwinns said, I also tend to wait until everything that I can see has come to a head. If it just sits under the skin I leave it alone, I've learned picking at something like that will make it spread. It's hard not picking especially after having been addicted to it for so long.
I used to pop mine all the time, but this ended up making my skin 10x worse, and because I'm pale the redness/inflammation would look awful. I'm trying to stop myself, but if I have an event I will pop them if they're really noticeable because otherwise I end up feeling really self-conscious. Or, I'll use a sterilised pin and prick the middle of the pimple, and use a cotton bud to gently squeeze the pus out (I know, ew!), but leave the top of the pimple intact. I find this makes them less noticeable and it doesn't seem to make them spread, or give me any redness, and the pimple can then keep healing without me messing around with it too much.
Yes that is what I have learnt from experience. Popping pimple makes things worse because you might end up with another pimple somewhere else on your face. The logic is that while you are trying to pop the pimple, you end up pushing the pus and the toxins into your blood.
I wish I could NOT pick my pimples. They haven't caused me scarring, but they sure as heck cause more pimples! I think you're right in saying that removing the ick from inside the zit makes it go away faster, but it's just not worth the other pimples that I get as a result. Now, to try and convince myself of that when there's a big one just waiting to be popped on my face. haha.
