Well, I bought an iPad today.
Decided to go for it now, even though my chances of getting one with old enough firmware to jailbreak it were pretty slim.
I lucked out. Got it at a Target that has an Apple store just a block away - I figured they move their iPad inventory pretty slowly. Got it home to find 4.3.3 firmware. Jailbreak took 10 seconds, and now I'm download apps like mad. Sweet