1. Agree with Moose, that match against Aries was great. The one against Storm from BFG the same year is another contender.
2. Roode is 36 now. I consider 35-40 to be the typical "prime" years of a wrestler, so if Roode is going to make that jump, it pretty much has to be now. I think he's got all the ingredients needed to do well in the WWE, the charisma, the wrestling ability, but obviously it'd depend on what gimmick they'd give him.
3. No idea. I don't watch TNA, so I don't know what the options are.
4. Luckiest man in the world? Nah, somewhere there's a guy that either is or will be one day going out with Mila Kunis. THAT'S the luckiest man in the world.