So I just got off the phone with UA reservations and was told that the only way I could use two upgrade methods on passengers on a single PNR was to split the record.

Is this correct? I went ahead and split the record, but only because the agent had already backed out both upgrades (my goal was to change from to SWUs to 1 SWU and 1CR-1).
The agent also said that I could only request upgrades for all passengers on the PNR, not just one passenger.