re: Whats the point of buying a Rolex?

They're cool to have, and they last. Heirlooms that are passed down tend to be respected more by following generations if they have legitimate/inherent as well as sentimental value. There are also more resources for maintaining/restoring valuable things than simple things nobody intends to last decades.

It's a harder call to pour money into restoring a painting or a watch where the restoration will far exceed the value of the restored thing. That's not necessarily the case with nicer things.

It's not a value proposition, I'm not saying it's worth the money to originally purchase or to maintain, but I get it and I'm glad we have some stuff like that in our family and I'll probably try to do at least some of the same going forward.