Your wanting to do gear is not consistent with your concern about gyno.
First, try anastrozole by it self and see where that goes. This will let your natural T work a lot better. You might be surprised. You do not need much when not on gear. Take 1mg/day for two days (front loading), then on the second day after that, take 1/4 every third day. You can expect to feel the start of things in 7-10 days. Libido can respond quickly and if that is right, your E2 levels are good. Other changes to brain and thought patterns can take 2-3 months to complete. Tissue changes also take time. Most guys on TRT do well on 1mg/wk. You might want to work down in that direction... dose also depends on body weight.
Lowering E2 should lead to less SHBG, which will increase TF. And the reduced E2 will allow the HPTA to produce more LT --> more T. And less T will be lost to T-->E conversion. Your increased FT will have less interference from E at the T receptors.
With age, aromatization increases and SHBG increases. E increases and that down regs the HPTA, reducing LH and T production. Less TT, less TF and more E opposing the action of what FT is left. Some powerful synergies that cut both ways. Reduced your E2 and there are many positive synergistic things that will happen.
If you do gear, with your history, start the anastrozole right away.
Avoid letro, it can push your E really low and that can create problems and kill libido. The dose-response is not predictable... doing E2 lab work?
Anastrozole is self limiting in effect and is well understood. A very few are extremely sensitive to it and need to take about 8 times less. If your libido crashes, you know that you are perhaps overly sensitive to it. Otherwise, research on young normal males found that 1mg or 2mg/day did the same thing with E2=17. All that did was demo the self limiting action and did not establish what an effective dose is, only demonstrating that both doses were excessive and on the far side of a dose-response that had plateaued.