I skipped the School of Hard Knocks last year because it looked miserable, and I didn't think I'd ever get the holiday meta-achievement anyway. Sure enough, this year rolls around and it is the only achievement I am missing. It took about 8 hours of play, but now I have it.
First, let me agree that this is really a horrible achievement. To get it, you have to play a battleground badly. I love battlegrounds, so it's not because I'm a pure PVEer that I hate this achievement. I hate it because they make you play battlegrounds badly, thus making all your teammates angry at you. I hate it because it's hard to do on your own, and it's also hard to get a group together to do it as a group.
Second, let me point to the excellent guide on Cynwise's Battlefield Manual. It's a great guide to how to get the achievement.
Here's how the achievement went for me.
Eye of the Storm. This was the hardest. It's only possible to capture a flag if your group controls the middle, and many teams don't try too hard to control the middle. Controlling three bases is better than making a bunch of flag runs. Basically I just persevered until finding a random group that zerged and held the middle. Then I could wait at the flagpole and click wildly whenever the flag was about to respawn.
Alterac Valley. I found this one pretty easy. I just ran up and down the set of towers until I found one that was held by the enemy but under contest. While other people finished off the enemy, I wildly clicked on the flag so as to get credit for it.
Arathi Basin. This one was pretty tough. The people playing to win want to hold the flags they have rather than trading them around. With no trades, however, there are no possible flags to convert. The final strategy that sort of worked for me was to follow around any zerg I could find, and try to be the first one to click the flag. It took many tries, though, and the other players were not really happy about this behavior.
Warsong Gulch. This one I thought would be easy, but was not. My original plan was to wait by the flag and simply kill anyone who tried to take it. However, I saw surprisingly few solo attempts on the flag, so it wasn't realistic for me to kill them. The only way I got this in the end was when some nice person from the opposite faction came and started picking up our flag and immediately dropping it. Despite about half the population of all the battlegrounds going for the achievement, this was the only player I saw doing that sort of thing.