OP, I am so so sorry for your loss. The subject of Disney and grief has been on my mind very much in the past few months as I lost my mother very suddenly in August, literally days before my partner and I were set to do online check in for our first cruise on the Wish, as part of our first land and sea trip. Mom was an avid cruiser and and we enjoyed WDW as a family growing up (though we stopped going when I hit my teen years, we did go one last time in 2016). We talked every day on the phone about the cruise, since doing a land and sea Disney trip was something she always wanted. We never got the chance. I struggled with even continuing on with that trip, but Mom was always a very practical sort being retired military and would always tell me and my sister that she didn't want us wailing at her grave when she was gone, because "it's not like I'm gonna be there anyway". So we still went, the week after the second memorial we had for her up north for the folks who couldn't make it to the actual funeral down south, and I'm very glad I did.
I agree with all the sentiments that people process grief differently. I'm so grateful for our TA, who took the reins booking things for us that I normally would have handled, even for the WDW portion of the trip. My mind was just not right. It still isn't tbh. I thought about getting a celebration button simply stating "Mom" to wear to Epcot specifically because it was her favorite park, but in the end I decided against it. That trip was all about escapism and I absolutely would not have wanted to be reminded of it by CMs--I struggled sometimes with an irrational anger, and still do, that when I'm doing relatively okay all of a sudden someone very well meaning will bring up how hard it must be, etc. to show empathy and then I'm jolted back to the reality of my mom not being here anymore, and I end up feeling worse. The only time I ever voluntarily talked about it was the last night at dinner on the Wish. Our tablemates were kind and compassionate (they were great ladies in general) but I'm glad that was the extent of it.
I don't think there's a right or wrong way to handle it. Best imo to acknowledge the statement, offer a brief condolence, and keep it moving in a professional way. When I trained customer service agents in my previous role at work, that was SOP. Insensitive questions are inappropriate though, and I'm glad you wrote to guest services about that.
