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Exactly, but why not amend PS into a 401k and avoid the added expense of plan termination and new plan implementation? Having an asset base at the start may help 401k pricing as well.

I suspect that there is no guidance on this interesting question. My gut says to permit reimbursement of these expenses but only if accompanied by documentation from a medical provider that the extra flavorings are recommended in order for the patient to take the medicine. If the flavorings are already added (e.g., by a pharmacist) before delivery to the patient, I feel even more strongly that it is reimbursable.

401(k)(10) - the rule is specific to 401(k) plans having successors.

If you have a copy of the plan document read it very carefully and see if it authorizes the Plan Administrator to do interim valuations at their discretion. Most plans documents allow for it and it is just for that kind of situation. There is a good chance they are all good. But it is very dependent on how the plan document was written before they did the interim valuation. If you search this forum you will find a bunch of threads on this very topic from that time period. That might help you get more background on the topic and the issues people were talking about back as Covid started to hit the markets.

This depends on how the document is written. The document will tell you if the match is based on the pay period (no true up) or plan year (true up) or some other method like quarterly, but that is more rare with our clients. If the document says the match is based on the plan year, then yes, you have to true up based on annual compensation and deferrals. This statement is not adding up, maybe I am misunderstanding the way you use "safe harbor". But a 3% match does not qualify as a safe harbor match in terms of ADP/ACP safe harbor.

Green - this is the key, it is not usually automatic (read the document) that all members of a CG are covered by a plan, usually each separate affiliated employer must adopt as a participating employer. If not, no employees or owner comp from non-participating companies can be included for contribution determination (but included for coverage and nondiscrimination).

Assuming all companies have adopted the plan and the plans definition of compensation is total comp, yes the sum of his comp from all 3 companies is what you would use for allocation compensation, subject to the 401(a)(17) limit.

Don't know whether this changes the analysis or not, but I think the OP meant to say "not TopHeavy".

Qualified Plan Roth money is subject to RMD rules, so yes RMD required. Assuming he meets the 5 year rule it's a qualified distribution so no taxable (and not eligible for rollover) but it needs to leave the Plan. If he has less than 5 years then the gains would be taxable but basis not. Unlike IRAs it's not first in first out, it's ratable. To avoid future RMDs, roll the ROTH potion from the Qualified Plan to the ROTH IRA (after taking this year's RMD) and before December 31.

IMHO: 1. Transfer (trustee to trustee) - it's only a RO if person has ability to receive, which is not the case. 2. N/A for transfer of this sort, reported on 5500s. 3. Yes, transfer. 4. Yes, and remember it is due by end of 7th month following the month assets went to zero.