He sounds like a very reasonable guy. I think testing your HPT via Clomid is a good idea, just to make sure that there's nothing unexpected happening. I would, however, make one suggestion: don't take the arimidex. I don't think he thought that one through very well. Allow me to explain myself:
As you know, every medication has associated risks. A medication is used when the benefits outweigh the risks. If your doctor's suspicion is correct (which happens to be my suspicion as well), and excessive conversion of T to E2 in adipose tissue is your problem, it will self correct as you lose weight. You are losing weight very quickly right now; supposing that you've got around 100 lbs to lose to reach your target weight, and supposing also that you end up averaging 3 lbs per week, that means that you'll reach your target weight in about eight months.
So the question then becomes: is the risk associated with arimidex worth the benefit you could get for this eight month period? Some background first.
Taking arimidex was easily the biggest mistake I've ever made, in all my life. I took it for about three months, at a very low dosage. I noticed pain by the second month, in my wrists. I discontinued all arimidex by the third month. The pain steadily continued to grow for several months until I could not use my hands at all.
I saw a rheumatologist, who diagnosed me via MRI with severe bilateral DeQuervain's tenosynovitis. As you know, tendons heal very slowly due to low blood flow; it is not uncommon for tendons to take a year to fully heal. I did not see any improvements for a full 10 months. I am currently at the 15 month mark. I still have pain when using my thumbs; I use speech-to-text software to use the computer.
Here's the bottom line: arimidex is a breast-cancer drug, so virtually all studies have been done on women taking 1mg per day. More than half of them will get joint pain, and the most common site of pain is in the wrists (and by extension, the hands) (see:
A prospective study of aromatase inhibitor-associated... [Cancer. 2010] - PubMed - NCBI). Pain is often very severe; rated as 8 or 9 on the pain scale. Many women with breast cancer choose to stop taking the arimidex because of this severe pain, despite the fact that not taking it puts their lives at risk.
You are a dentist; if you get the same wrist / thumb problem that so many people taking arimidex get (myself included), then you are done being a dentist for a year or longer. Thus, for eight months of better T levels, you are risking your livelihood, and your family's livelihood.
So is it worth risking severe, long-term pain in your hands for a benefit that your body will naturally achieve within an eight month window, especially considering the very high incidence of side effects? Absolutely not. This idea is myopic at best, and very foolish at worst...