1.) When using tiptronic mode, and shifting up from gear 1 to gear 2(At about 5500rpms)--->sometimes happens from 2-3 around the same Rpms, sometimes the shift doesnt shift cleanly and the car vibrates, i let off the gas, and its fine. Does this mean that I need a transmission flush ?(Dont remember when the last time it was done).

 

Try it and see if it does the trick.

And if you don't know the last time it was done then you should do it anyways.