I can't help with much of the rest of your questions. TT levels vary from person to person so there's not one answer as to what 100, 150, or 300mg will do to your test levels.
At that high of bf, you'll have a hard time controlling e2, but you're with imt and they know what they're doing.
Edit: This is just my opinion and others may disagree, but if you're really gyno prone, maybe talk to them about raloxefene, or something else that will bind to mammary gland and prevent the estrogen from binding. At least until you're competely lined out on your ai dose. Also, my terminology on how that process actually takes place might be off or at least simplified a little.