Dont ever let someone else, be it me, your coach or anyone, tell you to take more gear than you feel comfortable with. Sounds like you have some expereince and you know what works for you. That being said, its not a crazy cycle for someone that is used to running this amount of gear. Still, this is all individual. I dont know what your history looks like. There are some things I dont like about your plan though. More size is nice, but the goal here is to really be your best for the show. You are not going to make head turning gains in the first 8 wks of a contest prep. Even if you are eating more, you should still be trying to get tighter. So its not like it will be a true off season gaining period. So since the show is the goal, you do want to stack your gear toward the show. And as for cutting test out, it all depends on how you look. Most everyone I work with is fine to leave test in all the way to the show and they can still be diabolically conditioned. I might want to increase AI as I closed in but in general, using test, tren, win, I would set it up like this for a 16 wk plan...keep in mind, Im counting backward to the show, So wk 16 is the first wk of the prep. Wk 1 is the week of the show. You didnt mention doses so I dont want to include them since I dont know what you normally use

Wk 16-1

Test E

Adex- Like I said, possibly increasing the last few wks 

Wk 8-1

Tren Ace

Wk 6-1

Winstrol 

I also will use clen and T3 when and where needed but I use the least amount of T3 possible, starting further on if and when thyroid slows. Water should be low if you are super lean and any remaining water can be adjusted through the final week cut. But this is just how I would do it and it takes actually doing it to make it come together. Each diet and each athlete is different. Its all going to be about nutrition. If you have good genetics, thats a bonus, but make sure you are the leanest guy on stage and that will come through a good diet plan