Originally Posted by
FBinNY
The headsets that annoy me the most are those with cups at both ends of the head tube. That means flipping the bike, fitting the fork, then turning it back over on the ground (while holding the fork in), and loading the upper race and finishing the job.
That is exactly what he is dealing with. I have found that with Phil or other thick enough grease the small balls used for a headset will stay in even with the cup upside down, so there's no reason to have to flip the bike back - just leave upside down and proceed as I suggested - even easier with caged bearings.