I don't know how experienced you are, but this looks like a cycle I would have dreamed up when I was new to steroids. I would plan out a months-long cycle of non-steroidal supplements that I would be meant to lead up to an actual cycle of steroids. You are WAY over-doing this cycle, just like I always did. I don't mean you're doses are too high, you are actually showing impressive restraint. A better way to put it would be that you are over-thinking this cycle.
I suggest you decide whether you're going to add test and/or tren and/or winstrol or not. If you're going to use them, then I suggest cutting out the first 12 weeks of your cycle. And if you're going to use aas, I suggest sticking with tren and test, and, frankly, dropping the winstrol. All these extras are unnecessary, unless you are an extremely advanced user seeking every possible advantage, however small. Which is what I once did myself
Ironically, though I can no longer consider myself an advanced user (I've been out of the game a while) years ago, by the time I actually became an advanced user, I had dropped all the extras. I simply went with test and tren every time, an eca stack, a little arimidex and a little clomid (for gyno, no hope of stimulating test production while on those aas, except with hcg.) My post cycle therapy consisted of arimidex (tapering off quickly) and clomid (which I would stay on for a while.) And it worked. Really, really well. I kept track of my blood pressure, if it got high i cut back on the eca, or increased the arimidex, or both. Now, at the time there wasn't anything effective around for prolactin, so maybe today I would add something in if I had the money.
Just because that worked for me doesn't mean it was ideal, or that it was the absolute best I could possibly do. But then, there's no such thing as the perfect cycle. You are clearly (admirably) concerned about side effects, but if you're going to use aas, there are simply going to be side effects. You can prevent some, but you can't escape all of them.