Beautiful post. Thank you for starting a thread NOT about waitlists and investment value. Yours is a great story, albeit sad, as I cannot imagine losing my parents at such a young age. At least you have things to remind you of them, and you remember them fondly.
My most sentimental watch is not a Rolex, it's the Omega AquaTerra that my wife gave me as a wedding gift 14 years ago. I wore it at our wedding and throughout our honeymoon, and because it's the closest thing that I have to a dress watch I end up wearing it during special occasions, so it has a lot of memories with us.
Watches that I buy for myself just don't have that same sentimental value. They all come and go eventually, but that AquaTerra will always be with me.