Do you have the 2F-type distributor clamp? I've broke two of those clamp bolts, and I don't trust old ones.
If your assistant will crank the engine, with a socket in the crank, or with the fan belt, or with the starter and the coil disconnected from the ignition switch, you can push down on the distributor body and the driving tang on the end of the distributor will mate with the oil pump in less than 180-degrees of turn. I've never done it this way.
The fender is in the way, often, but, if you can see from the fender's perspective (using a mirror)...
View attachment 3807092
There is about 1/4-inch engagement with the distributor shaft tang and the oil pump.