I'd get an AI (Adex or better, Aromasin) + Prami or Caber, pretty quick and drop the Clomid/Nolva for now. Progestin gyno is said to start when Progesterone and Estro are both present. So without knowing the whole picture, I'd cover both angles to be sure. And Nolvadex is thought to worsen gyno from Progestins. So Id leave Nolva out alltogether.
I say this because those other compounds, especially Winny and Mast should almost leave you with zero chance of Gyno, even without a SERM.
So IMO, the most obvious suspect is the use of Tren + higher levels of Estrogen from coming off cycle. Exemestane + Prami for a bit is what I'd do. And Clomid without Nolva, later.