Special gift for $2000 range

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Is there any specific item he wore personally that might be of personal significance to her? I'd find out about that first. She might really love his watch or some ring he wore and having that sized to fit her might mean more than a new item. My grandpa died on the 2nd of January and having his watch was more important to me than anything else. It's nothing special as far as a brand, just something like a Timex or something, but he wore it and I know HE wore it.
 
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I wish there was something with significance behind it that I could give to her and I have a box with all of his special belongings. DD does not seem interested in his watch. I even asked her one day if there was something that she thought of when she thought of him. Then, I asked about a couple pieces of Tiffany items, she wanted my uncle to pick. He is mentally there and communicates but I know there is no way for him to make a decision.

He also lives in NYC, maybe something with the city that could be connected.
 
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