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Well first off, you don't mention anything about AI's - so if you're looking to combat water retention and bloat from highly estrogenic compounds go with an AI. I'm all for maximizing synergy when creating cycles and choosing certain drugs based on the pathway, so I think theoretically you're headed down the right road. Frankly, I think winstrol is a terrible choice as an off season drug. I'm not one to use certain drugs if I'm not going to experience the whole package that's why I'll typically only utilize certain DHT based drugs during a prep. And if you're looking for synergy as you say I think there are better DHT choices - and I'd also question the use of Tren and Deca, I'd probably switch one out for something else. I'm also never a huge fan of orals in the off season, so I'm going to be a little biased. Sometimes to get through a plateau but most times I think of them as overkill or just unnecessary.