I have a couple of real automatic watches (Bulova automatic, vintage Seiko automatic) that should still be around and working when I die. Of course, they'll be passed on to the nephew as I have no kids. Also, my writing utensils (Waterman pens and others) should still be around. Obvious;y they'll need refills. Oh, and I wear the Bulova and carry one of the Waterman sets with me, so they are daily usage items.
Woodworking tools like some old hand planes and draw knives, a quality chisel set, and my lathe chisels that, assuming they are cared for, while not daily use, get regular use and will be passed down to the next generation of woodworkers I know.
But, except for the watch and pens and a few quality hand tools I've personally bought, most of what I will pass down are already antiques either bought as collectibles or passed down to me from my parents or grandparents. I do have my grandfathers Ryobi rotary tool and it works great, but it's probably only 10 or 12 years old. I doubt the motor in it will last to see my passing no matter how well I maintain it.
@abge - Have the Citizen thoroughly checke dout every 5 years and it should last a couple of lifetimes. While not my favorite as it still has a battery, the Eco-drive movement is still a solid movement. But if you are willing to spend $400 at some point in the future, the Bulova autmoatics are world class and nearly as good as watches 10x their price. The best under 10 grand, of course, is an Omega, but that will still cost you $4000 (yes 4K).