I have mapped hundreds of TFSI based cars with Revo, even with 'incorrect' settings I have never had a DSG issue like you are describing. 2008 cars don't tend to have many DSG issues, I would flash to stock and go from there.
Fuel octane won't really affect much, might be worth Pulling the spark plugs and checking them, and replacing ith new for good measure.
You mentioned it all started after first tank of vpower, did you run the tank extremely close to empty? Had an Audi A5 in recently that ran extremely low on fuel and then started playing up, new fuel filter solved it.