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If a candidate has two Academy Appointments but is waiting for a medical waiver from both can he accept both appointments until he knows if one or the other will give him a waiver?

Difficult decision and could use some input for my DS. He underwent knee surgery and has recovered completely but DODMEB won't accept release until 90 days post op which will in 2 weeks. (his physician already cleared him) Today he sent in his acceptance for the Naval Academy and then 4 hours...