Originally Posted by Zorak

The DL policy on complimentary upgrades with companions is:

1. Medallion + one companion in the reservation are eligible for and treated (for upgrade purposes) as the status of the Medallion
2. with multiple companions on one reservation, eligible for upgrade IF everyone is a Medallion (priority depends on how you check in)
3. with multiple companions on one reservation if anyone is a general member, then no one is eligible
4. Medallion + one companion on separate reservations clear at their respective priorities (general companion member clears 24 hours out at the earliest)

This is why you were initially ineligible on the same reservation (multiple companions, general members) but you + son became eligible when your husband was split out.

The last point is also probably what the agent was thinking of when they told you your husband might clear but no sooner than 24 hours. However I am skeptical that you can simultaneously apply (1) & (4) as a workaround to (3). A GA might do it for you as a favor but it runs counter to my interpretation of the rules.