I definitely paid with some time investment, but you bet I wrote a short script to automate toggling that rule on/off. It’s also not like I had to run that script every time I wanted to play a game. Only to play a game in my brother’s library while he was playing something else or when I wanted to play one of my games and he was already in one.

Summing up the time investment vs. the cost of games, and using a time-money conversion rate that assumes I had a well paying job in my field and wasn’t still a student, it was definitely profitable.

You’re definitely right on the frustration front though: I bought many games just to not have to deal with this. It was mostly used for games one of us was on the fence about. Or (like in the Outlast case) only one of us really wanting to play a game and the other just playing along because playing together is fun no matter the game.
Now, in the former case, it might be back to sailing the seas.