When I learned that a wheel-less early 1960s Capo Sieger with paint in far worse shape than mine just sold for $2K on eBay, I warned my wife and sons not to let my stuff go to cheaply.
My boys are 3 and 6 inches taller than I am, so my road bikes will be too small for them. If my elder son did not already have a Cannondale Rush (my graduation present to him), he might be interested in my classic red-white-and-blue Schwinn mountain bike. Right now his commuter is my 1980 Peugeot PKN-10, which was always a couple of cm too tall for me.
The boys will want most or all of the tools, since they grew up working on cars, bikes, appliances, and the house with me. Working on projects together is a great way to get your teenagers to open up and talk to you and grow into adults you value as friends.
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"Far and away the best prize that life offers is the chance to work hard at work worth doing." --Theodore Roosevelt
Capo: 1959 Modell Campagnolo, S/N 40324; 1960 Sieger (2), S/N 42624, 42597
Carlton: 1962 Franco Suisse, S/N K7911
Peugeot: 1970 UO-8, S/N 0010468
Bianchi: 1982 Campione d'Italia, S/N 1.M9914
Schwinn: 1988 Project KOM-10, S/N F804069