This is a source of great debate in the AOS forum. I've read tons of threads over there where this simple question turns into a huge argument between a bunch of know it all senior members. Basically, the general consensus is that there is really no legal consequences of filling AOS after the I-94 is expired, and technically there is no time frame you need to file AOS in. You can do it in 3 days, 3 weeks, 3 months, 3 years, 30 years, you still met the requirements of the visa- which was marriage within the 90 days. The problem is that until he files AOS, there is no evidence he is in the US legally. As far as getting a license, getting a job, and really starting his life in the US- the sooner he has evidence of status the better for him.
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