Wesley, if I understand things correctly, you crashed your E2 while taking too much AI, is that correct?
I've been there, and I can attest that the rebound doesn't always come back in timely fashion. For some guys it's just as simple as stopping the AI, continue TRT treatment and E2 converts downstream and rebounds quickly. For others it can take several months, as in my case. Why exactly that is (?), hard to say, as it could be a factor with 5-AR reductase activity, and/or possible metabolism factors associated with the liver. Unless some puts it under the scientific scope, it's mostly speculation, but it is a condition that can happen.
In my situation, I have some genetic issues related with hemochromatosis, and my liver function isn't all that optimal. Again, I can't confirm the correlation, but it's one of my theories considering the liver's role with regulation, methylation and metabolism of hormones.
There's been some discussion about the effects on the adrenals. First, as you've experienced, you start to find out just how important estrogen can be when you DON'T have any! For me, my immune system was a wreck for several months, where I probably caught 3 to 4 colds. I've been used to the 1x per year if that. Nails get weak, hair looks like crap, skin tone sucks, and yes it has an effect on cortisol and the adrenals. If that kicks in then there could be further effects across the way with thyroid activity, and increased Reverse T3 and suppression of ATP. The best thing to measure this is labs and a good physician!
I wish I could tell you that it will be real soon ... I can't. Possibly it will be right around the corner, or possibly it will take longer. Since you're on TRT, I recommend that you only inject 1x per week, and maybe with your physician's guidance you can get your serum up a little more to help promote more E2 conversion.
I'm sure you have heard to eat soy, flax and all that stuff, I won't reiterate it. However, I would highly encourage that you maintain a positive diet with lots of vegetables, protein, and make sure you get ample amounts of minerals and vitamins. I will say this, when it starts rebounding at a steady rate you might experience some overly sensitive activity with the receptors in the nipple region. It's not uncommon during the rebound so don't wig out. Talk to your physician about having a little Nolvadex/Tamox on hand, and little meaning 10mg/day can in most cases mitigate the E2 sensitivity issues (just my opinion). It's actually a good thing when you get to that stage, as you then know that your E2 is making a comeback!
Hang in there and stay patient!!