In the end I'm not saying that would be a huge problem in that it would basically just jump us ahead 2 weeks but how possible is that for someone to pull off? It seems like a pretty good sized vulnerability. Especially if a couple large miners all decided to do it.
Doesn't seem simple to pull off:
A timestamp is accepted as valid if it is greater than the median timestamp of previous 11 blocks, and less than the network-adjusted time + 2 hours. "Network-adjusted time" is the median of the timestamps returned by all nodes connected to you.
So to set a block's time considerably into the future one would have to control quite a portion of the network (>50%?), it seems. On the other hand, you don't seem to need to have a lot of compute power, if any.
Unfortunately for the attacker:
Network time is never adjusted more than 70 minutes from local system time, however.
So it seems quite impossible to pull off setting a block's timestamp into the future considerably.