Save the Winny for the end of your cycle. I would run it like this:
weeks 1-10 Test E @500mg
weeks 9-12 Winny 30mg/day
That way you can go right into your PCT the day after you take your last Winny tabs. No need to take the Winny to kickstart IMO.
A friend gave me a whole bunch of Testim gel tubes. If you read the insert carefully it says that only about 10% of the testosterone you apply gets absorbed and makes it into circulation. So 50mg = only about 5mg acually being absorbed.