Cheap GM's? I had one that took the cake...
He had us cut press releases and other station mail into 3X5 pieces and used the blank reverse sides for phone messages.
He wanted me to call other area radio stations to attempt trading our shorter carts for longer ones instead of having the ones we had re-packed or buying new ones.
He refused to invest in any additional remote equipment despite a big push to do sales remotes and appearances. We had a card table, a traded out banner, some really old bumper stickers and a Marti & yagi (which came with the station when he bought it a few years earlier.) That's it. Not even a crude PA system and no station vehicle, not even traded out.
He gave me no budget for music, and we got little record service since the station was very small. He wanted me to make copies of songs from the other radio stations I did p/t for on reel-to-reel (recycled, of course), bring them in and cart them up for our air. This was a trend...wanting me to steal from other stations. I told him I saw a copy of the latest Arb book at my p/t station and his station actually appeared! He wanted me to make copies of the BOOK and bring it in.
I told him we needed a CD player for the production room (this was around 1990) so he brought in the one from his wife's stereo in her office at home ("She doesn't use it anyway").
He cancelled all the newspaper subscriptions along with the AP wire service, and told the news staff to "listen to the big, regional news station for the area on the way into work to get the top stories", then rewrite them for our air.
I could just keep going......