Just wanted to add that I am also having this issue with the freelance programmer career. Closing out the game and reloading provides a (very) temporary fix but the minute my sim travels anywhere and then tries to do anymore work, the tasks go unchecked everytime.
I've also found out that if you sell all your computers in buy mode when you are doing an action then undo the sell you will be able to reset your computer related gig tasks but won't lose the upgrades you have on your machine. For example, encrypt files reset when I did this. Hope this helps someone out.
@WhisperPntr I mean I can see how that would be handy in this context but.... isn't that a bug in on itself?
