Hey Bro,
If you have not run Tren before, start with Tren Ace, so that you can see how it effects you and you'll be able to control it, if the side effects become too harsh. Tren ace has a half life of just a couple of days. If you have issues with Tren E, it can take weeks to get releif. Plus ace will start working fast. I'd start with 50mg EOD and move to up to 100mg EOD at the most, after 3-4 wks.
With your winstrol, I'd run it for the last 6 wks, 8 wks at most. Hard on cholesterol and liver.
For your HCG, 250iu 2x wk through the cycle, then STOP using when PCT starts. You can't begin to recover until you are no longer using it and you give your body a chance to begin producing on it's own. Work hard and remember that it's the diet that will get you to your goals! Best of luck, bud
For EQ, I would take at least 400mg. 300mg is too weak IMO. Its a great drug IME, but mild and I don't think you'll get much effect off of 300mg
Last, at 44 yrs old, you may have a harder time recovering from gear than when you were 24. Tren can be especailly hard to recover from, so be aware, the more you cycle and the longer you run it, the harder it will be to recover. Really, you could do just fine without the tren. If you are new to gear, Test/EQ/Win is a hefty cycle, especially when you have never taken 2 of them before.