So I talked both with VW credit as well as my dealer about buying out lease options.
VW credit is very black and white and what they see on the contract is how it is. So, whatever you owe left on the lease + the residual value set by VW on the date of purchase is what you pay to buy out the car. There is also some like $350 fee or something lame like that. There's no negotiations, and it's a very simple process. You can even get a "pay off quote" online anytime by signing in to your account.
My dealer said pretty much the same thing. I was a little set back though b/c I recall them saying that the residual value is negotiable in the end if you decide to buy out. What he did say though, is that if I decide to trade in the lease for a newer 2015/16 GTI that the trade in value is negotiable.
Also, if you buy out in the end, it does not matter what your mileage is...even if it is over the terms of the lease. There will not be a fine for that, unless you turn the car (don't decide to buy) in with miles over the limit. Good peace of mind.
So, what I've determined from this is that it does not matter what time you your lease out. To VW or the dealer it will be the same amount of money in their pockets. However, if you need to take out a bank loan to buy out the vehicle (which I would) you have to look at the amount of interest you'd be paying on the remaining balance of the car now as opposed to the end of the lease, whenever that is. You can also compare to your current payment and do all different variations to figure out the best time for you. I'll do all this for my finances eventually but right now I'm fine with just paying the lease as is!