I grew up in the deep suburbs, the kind where children could go out in their bicycles at night unescorted and minors like me and my friends could take our rifles to the local dam/reservoir to hunt game. Growing up our family home was home base, a refuge. If everything fell apart, I could always go home. And I thought that family home would be sort of an heirloom to me and my siblings.
Decades later my parents moved to NYC for work and when it was our time to work, me and my siblings also moved to the city. Our area was re-zoned for mixed use. Our neighbors houses were torn down to become apartment buildings, auto repair shops, etc. Our house was rented out and used as a day-care center. I was away but the houses I bought and lived in, I repainted all the rooms to have the same color scheme as the house I grew up in. And in the back of my mind, I always knew that at the end of the day we would end the lease and if we wanted to still be able to come back home.
After a few more decades, back property taxes, unauthorized unpermitted construction at our house (to extend the amount of day care space), my parents decided taking back the house and restoring it was more time, effort, and money than they wanted to spend. So they sold it. I was shocked and one of my sisters was upset for a very long time. My parents tried to make up for this fiasco by giving out our "inheritance", basically the proceeds of the house. But I didn't want the money, I wanted my childhood home.
So even with the best of intentions, heirlooms get lost. For many different reasons. Every day online I see watches with family inscriptions and dedications that probably should never have been available to the market for strangers like us to buy, yet it happens. So the best I can do at least is to choose something that will require the least amount of effort for my heirs to keep in the family. What has a personal attachment is something that can be 100% controlled. If at the outset you decide to buy a Rolex / Omega for your wrist, or a Timex or JLC - in time either will develop the same amount of attachment to your wrist. But not all of them will be as easy to keep in the family.