One possibility for no oil at the top end is under the sidecover there should be an 1/8"NPT plug near the middle of the block, and in some cases another one towards the rear, above the rear cam bearing. This applies to 58-62 blocks. Earlier blocks used an oil line to connect the two holes.
Sometimes people forget to install the plugs when rebuilding.
Take a look at the top of the long head bolts (remove valve cover). Do any of them have an "O" marked on them?
Not sure that you would necessarily get a reading on the gauge with such low rpms like you get from a drill. I can't remember if I got a reading on mine the last time I did this or not. Lets concentrate on the top end first...
