You sound like the test is just a 'throw in' to the main winny cycle. It should be the other way around. Don't make the oral the focus.
I would up the test to 500+ (depending on stats/exp) and drop the winny to 4 to 6 weeks. You could up the winny dosage some if you are tolerating it well, but it is one of the harsher orals on your cholesterol/bp. Basically, the winny should be the cycle 'throw in'.
As for the aromisin, it's needed if you start to feel any nip soreness. At the levels you laid out (200-300 test/50 winny) I would be surprised if you needed it unless you are sensitive to gyno. You could always take a low dose (12.5/day) just to be safe.