I love testosterone. I think if you're doing TRT, you should do it at around 125 mg a week. If you're doing a cycle, you can go ahead and blast it up to 500 mg a week. If you go high, you need an AI and you should have an AI on hand regardless.
I would not stack Winstrol with anything too harsh and if you do stack it with something harsh, run it at a low dosage. I would stack it with maybe a little testosterone or maybe some primo.
When it comes to anavar you can certainly kickstart it but I'd also consider using it toward the end of a cycle too. It has a lot of different benefits.