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I think the location of the assets is 100% irrelevant.

I agree with David but good merger amendments/resolutions will specify that the assets in the old plan are part of the surviving plan as of the merger date.

I shudder to think how common this type of thing is.

If what the executive seeks to do is to release the charitable organization from all or some of the organization’s obligation to pay her deferred compensation, the charity should get advice from its lawyers and accountants and the individual should get advice from her lawyer and her accountant. They might consider: How to document the release? What accounting notes to put in the charity’s financial statements? How the release would affect the next IRS Form 990 information return? What tax information reporting is required or permitted? If tax reporting is by a service provider rather than by the employer directly, what notices and instructions must or should be given under the service agreement? How to value the release? (Consider whether the value of the release might be less than the amount of the obligation released because the value might be discounted by the probability that the organization would not pay the deferred compensation when and as due under the plan’s provisions.) This is not advice to anyone.

Probably not. Was one of the businesses the result of a recent transaction that would fall under 410(b)(6)(C)? If not, and if they are a controlled group or affiliated service group, then you don’t combine for 415. Instead, all the SIMPLE contributions are all treated as excess IRA contributions for the years in which both plans are in effect.