My vote goes for Cycle #1. There is not much difference, but I think it would be advantageous to use Tren from day one for immediate strength gains. Tren will act as a nice kickstart to your cycle. After you get off of the Tren, the Winny should make up for any strength loss. I will be doing something similar:
Test E (650-700 mg/wk) 1-12
Tren (90 mg/eod) 1-8 (I have 40 ml and may just use it all, depending on how I react to it)
Winny (50 mg/ed) 8-14