Well TRT is usually intended for the long haul for a purpose, being shutdown for six months may take some time to come back from, and 100 mg/wk seems a small dose to be worthwhile.
Taper off the arimidex after you stop taking the test and as the test begins to clear (however long that is for cyp, I imagine around 2 weeks). Arimidex needs to be taken daily or EOD, im not sure how you have been doing it but I would suggest working down to .25 mg a 3x week 1, then 2 times week two. You don't need to worry about an estrogen rebound per se, there will probably be a little extra aromatase enzyme floating around upon cessation, but so long as there isn't extra test to convert it shouldn't be a big deal. If you are really frightened you can find some aromasin and take it instead to kill off the enzymes, as that is how that drug controls aromatisation, rather than blocking it at the site, but I don't suppose it would be necessary.
I would definitely recommend HCG, 250-500iu 2x/wk along with your clomids and nolvas for as long as you deem necessary. I can't give any input on the time frame you can expect, but it may be lengthy.
wish I could be more helpful.