It's tricky having a theme of 'mind numbing repetition ' and not accidentally making the game itself uninteresting, but you've managed to thread the needle here. Well done!
In my game, I managed to get all the permanent prestige skills maxed (except crypto, which was at lvl10) by the end of my second job. On my third job, however, passive income went down to $1/sec and all my temporary skills showed as still being maxed out but didn't activate any benefits. It seems like the upgrades all reset (except passive earning, which reset to the lowest purchasable level) but the upgrade menu didn't.