Personally I would go a different route. I would all out bulk for the first cycle, forget the winny and front load with prop or suspension for the first 4-5 weeks. I prefer to use an oral for the front load but if you are against them then prop or suspension would be the way to go. Not that running winny on the tail end is bad, its just that I feel the first cycle should be memorable and fun. And for me, a full out, all items on the menu, forget cardio, bulk till I cant scratch my back at all and need help taking off my gym shirt cycle is as good as they come. That being said, if you are on a time line for a vacation or need to look your best for the beach in the near future etc, then you probably wont want to sacrifice your midsection as much.
I'm a firm believer in HCG for every cycle beginning around the 4th week (depending on the compounds) but you're going to see varying opinions there as well. In my experience Ive recovered much more quickly using it on cycle and then doing PCT than not using it at all. Given the cost to benefit ratio of HCG I really don't see an argument against using it.
Also test E will be detectable for around 3 months, however most drug tests don't check for AAS.