It is a difficult one, I gotta say. I mean, 10 iterations is more practical. If 20 out of 40 iterations show hit to be superior to intellect, this makes me wonder how useful simulating hit rating at 10000 iterations actually is. We're not going to kill a boss fight 10000 times. It is likely one week we will miss loads, the next not much at all. We simply cannot predict what will happen. My instincts tell me we can't really win either way - we get to the hit cap with lower intellect and risk lower overall damage. Or, we go for intellect instead, being under the hit cap but risking those 'bad nights'.
I personally think that you should get as close as you can by reforging, then just leave it. I don't think it is worth gemming/enchanting hit unless you are nowhere near the cap (anything under 14% maybe). It's too uncertain to both be going crazy with it, and ignoring it completely.