Originally Posted by
HillRider
The following is by far the easiest headset bearing installation procedure:
1. Drive out old headset cups and crown race and discard.
2. Purchase proper size cartridge bearing headset.
3. Install new headset cups and crown race.
4. Install bearing cartridges oriented correctly.
5. Install top race cap and locknut.
6. Adjust headset and tighten locknut.
7. Come back in 5 to 10 years and repeat.
It's an approach, but then again my loose ball headsets last just about as long, with about the same effort. It's also kinda expensive for an older bike (pre-which war?). Then there's a good chance that the head tube and fork crown diameters are different than modern stuff, taking this option off the table.
Generally headset service is similar to all other bike repair issues. Easy if you know how, not so easy if you don't. Other than getting grease on my fingers, I don't see how setting up a cup/cone headset is any harder than a cartridge bearing one.