My test was at 257 in June before I started Clomid 25mg a day, by July my testosterone was at 797 (fasting, no Clomid that morning). I just got tested again last week and I was up to 875 (also fasting).

All I can tell you is that I feel great. My minor aches and pains are gone, my major aches and pains are now minor, I'm getting strength back in the gym, body fat is going down, muscle mass is up.

Clomid deserve a try since it boost your natty test, test injection for trt supress it for good after a wile, as whynot said, it doesn't work for everyone, he should know after few month.
I don't see the point of using AI, unless his test level get very hight so the Estro, i don't think it will be a problem.

The only way to really answer that question is to get a blood test and to see if his E2 is elevated and where his testosterone level is. Some people respond really well to clomid and can get up to a level of greater than 1500, in a case like that an AI would be warranted. For others Clomid does absolutely nothing. So it's a very individualistic thing and the only way to really know is blood work.