The "in one session" achievements are weird, because they don't actually get seem to have to get triggered in one session. Yesterday I was playing the game for a while, switched it off, put it back on later, and decided to go for the "break 50 chairs and tables in one session" achievement. So I booked an Extreme Rules match between Cody Rhodes and Booker T and Cody went to work. I broke ten chairs, and got the schievement, even though it was the first match in the session.
Need to start booking Edge now to get the secret achievement for him.
I don't chase really obscure achievements like the ones which require you to collect 250 flags scattered around a city, stuff like that, but I will go after ones I think I might have fun in getting. Like on Forza 4 there's one for doing 88mph in a Delorean, which I have got, but another for owning every Ferrari on Disc1 of the game, which would require you to do a stupid amount of racing to earn the money to do. I won't bother with that one.