RE: 2.0T + chip + dsg = problems?
 

yeah, that was what i was thinking and i looked it up, with the stock rims, the biggest it'll get are 235's. besides, i have no intention on getting bigger tires for the current rims, i DO plan on getting bigger fatter rims once my current tires wear out.

RE: 2.0T + chip + dsg = problems?
 

I'm just letting you know what I have learned from years of national level competitive autocrossing experience.

Pirelli tires have a good name, but they aren't winning street tire class autocrosses either. Some tires to consider that might provide more grip: Michelin PS/2, BFG KD or KDW (the KDW is a bit more sane for street use) Kumho MX, and Falken Azenis (this one also not entirely sane for street use). The Michelin would be your best bet if comfort and noise are important to you as well as grip.

A slightly better tire compound will give you far more benefit than just a wider tire of the same type. Often times getting huge tires will give you a false sense of solving the traction problem, since the heavier tire and wheel is just harder for your engine to break loose now. You haven't really gained as much grip as you think.

That said, on a 3300lbs car with 260hp, 245s all around is perfectly reasonable. If I was trying to win an autocross Id even chop the fenders and put 285s all around, but for street use you may find though that 225s work fine too with a really sticky tire. Big tires have the downside of weight, and I assume the goal is mostly to be able to punch it in 1st and 2nd gear and not spin the tires like mad?

Some things to consider: stiffer engine mounts often work wonders on FWD cars grip off the line and preventing wheel hop. Lower suspension (and to a lesser extent, stiffer) will reduce weight transfer and give the front tires more weight to work with. An LSD will help utilize both front tires better as well.