Anyone know of any tent models that includes the following:
1. Large vestibule a la Hilleberg GT models
2. Is freestanding
3. Can be set up from the outside with the rain fly on
4. Is around 2kg or under for a 2 man tent
5. Is not single walled (though i would consider it if it was the only option)

Right now my two options are Hilleberg anjan gt or the msr hubba hubba with extended vestibule. However neither fill all my requirements.

Thanks in advance!

Does it need to be a Four Season tent?

The Kuiu Mountain Star looks like it meets most of your criteria:
1. Maybe not ideal--18 sq ft of vestibule space split up into two vestibules.
2. Yes
3. Yes
4. Yes, 3 lb - 10 oz, 1.65 kg by Kuiu's specs, packaged.
5. Yes

http://store.kuiu.com/mountain-star-2p-p/12002.htm

4 season is not a requirement

I have one of these and it is the best tent I've ever had, far better than MSR IMO (of which I've owned two): http://www.terra-nova.co.uk/tents-and-spares/all-tents/

What about a Stephenson's Warmlite? http://warmlite.com/warmlite-climbers-two-person-tent The 2CR meets all of your requirements, except it is not freestanding.