Sorry to resurrect an old thread, but I've had my OD quit working two or three times like this in the last year or so. It seemed to be a real hard drain on the charging system. If I pulled the OD fuse, it would charge normally. If I put the fuse back in, the OD would not engage and the charge system could not quite keep up. I bet if I drove for a couple of hours it would kill the battery.
How have I fixed it? I just let the car sit overnight, and the next day it works fine, every time. It will work fine for months sometimes before the problem comes back. Seems to be only when things get hot, but the other night, the car was not driven for more than 20 minutes and it was a cool evening.
Last summer I blamed my charging system and rebuilt the generator, new regulator too. Problem still happened after that.
I'm ok with letting it sit overnight for now. Just impressed that these 70 year old parts work at all lol. I've played with the relay, cleaned the connections and the points inside. Cleaned all the other connections in the whole OD system, everything is clean, clean clean. Had the solenoid apart, all is clean and works great most of the time. New kickdown switch.
Not complaining, just hoping to help someone else out if they are having similar issues.