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What is teh definition of comp for the plan? I don't think 1099 income falls under the any of the usual suspects: 415, simple 415, withholding, or W2.

For plan purposes, he is an IC because that is how the employer is treating him, even if the IC/EE is misclassified. As long as the employer treats him as an IC he is not an employee and therefore cannot participate.

I can't see how he could participate in the current 401(k) plan post 7/1 b/c he'd have no allowable wages from which to defer.

Actually, I was in a bit of a hurry, and I think I gave you bad information on the safe harbor piece. The deadline for the safe harbor piece is indeed 12/31/2016, to preserve the safe harbor status of the plan. However, for 415 purposes, since made after the 415 deadline discussed earlier, it is ALLOCATED for 2016, same as the profit sharing. Still only one deadline for 415 purposes. There are some limited exceptions to the otherwise applicable 415 deadlines, but this isn't one of them. Prior to the 2007 415 regulations, I seem to recall that the 12/31 deadline was used for 415 purposes as well (which frankly made sense) but the final 415 regulations didn't provides this carve out. Sorry about that.

... and some (like myself) who may provide a wealth of non-useful information.

jireh87 - Welcome. The best suggestion I can give you is that you read practically everything that's posted on BenefitsLink (except maybe not when they get into deep details about something about which you have no need or interest to know). This site has a boat load of experts who provide a wealth of useful, documented information.