Uplink
Here's a blast from the past: I remember playing the Mac version of this guy, what, almost a decade ago? At the time I got bored with how much of the game was point-and-click rather than keyboard-based. Now that I've got a shiny new copy from some past Humble Bundle (and now that I've got a beer in hand), I decided to give it another go -- and unfortunately stumbled into a basic design flaw that really ruins the whole experience.
The basic element of suspense in this style of game is the trace, where the target of your intrusion attempt will try to detect you. And although Uplink offers a wide array of purchaseable upgrades - faster processors and modems, more memory, cracking software with more features and power - there are no upgrades to reduce the speed or effectiveness of these traces. Instead, the only way to foil trace attempts is to connect through a large number of intermediate gateways, which makes the map crowded and useless, and even when you overcome the tediousness of clicking on dozens of relays, this feels like it dilutes what is otherwise the major challenge of the game.
I would also accuse the game's general balance and pacing of being really off: the credit rewards for individual missions are never enough to make significant progress, missions can only be done simultaneously in very rare instances, and to start, your reputation is so low that there are barely any missions available at all.
I am as interested as ever in the idea of a hacking game, but Uplink is just too unpolished to deliver what I would call an adequate experience.
Progress: Gave Up -- Became "Notorious"