Conservative is a relative term. Dropping transactions in a way that is unpredictable to the sender sounds incredibly drastic to me. I'm suggesting increasing the blocksize, drastic as it is, is the more conservative choice.
I would recommend that the fork take effect when some specific large supermajority of the pervious 1000 blocks indicate they have upgraded, as a safer alternative to a simple flag date, but I'm sure I wouldn't have to point out that option to people here.