1) Get bloodwork done to make sure there's no major health issues and go get a baseline.
2) For your first cycle, do test E 250mg a week for 12-16 weeks. If, 4-5 weeks in your liking it and don't have sides, bump it up to 500mg EW (but not more, the first time around)
3) For supports, I'd recommend the following for a basic cycle:
A nitrate product
DHA/EPA fish oil
Antaeus Talos
Antaeus Ultra CoQ10
Antaeus Achilles (based on your age, in case you have any joint problems; you don't want that ruining you cycle)
Exemstane (12.5mg EOD is a good starting point, stick with this from day one and at least 2 weeks after your done with PCT, then taper off)
HCG (500mcg every week). This is optional.
Clomid 25mg ED for 6 weeks as a PCT.
4) Around week 10 of your cycle, when you've been on the same dose of exemstane and test for at least 4 weeks, get bloodwork done again. This will tell you how the cycle is affecting your health, and give you an idea of your hormone levels
5) 6 weeks after your done with PCT, get bloodwork again. Now you'll have a complete picture of your health and hormone levels before, during and after a cycle. While other cycles will be different, you'll be able to gauge much better.