I see your point. The Regs, when written, seemed to have made it a point to use a date within a calendar year for their example. It's never going to be an issue whether you offset a loan on October 5th (for example) instead of September 30th. When you're crossing tax years, then it issue becomes whether it is a hard-fast line in the sand for tax purposes. I don't think it would be egregious enough to warrant this level of scrutiny given a process that has been designed to meet the 72(t) standard. The issue comes into play, in my mind, when you look back and determine (in retrospect) that you would've faired better had the amounts been taxable in an earlier year than the one reported. At the end of the day, the amount (at the time of offset), whether December 31st or early in January, could've avoided all taxation had it been rolled over to an IRA. Remember, at the point of offset, it's not a deemed distribution, but an actual distribution. I see you're point, but this is the absolute FIRST time I've ever heard of a situation where a participant is arguing for an earlier 1099R; when all could've been avoided by merely paying rolling over the loan (or requesting the loan offset distribution at the time the employment terminated). One thing that will always been constant in our industry, however, is that these types of issues will always exist at the lines where one period ends and another period begins. We recently had Regulations on post-severance Compensation because of deferrals made by employees who terminated late in the Calendar year. It's always going to be an imperfect process. I'm not suggesting to undermine any rules (even though it may appear to be that way), but this is a one-off that could've been easily avoided.
Good Luck!