I distinctly remember that Wing Commander had "good guys" not winning paths. My second most frustrating experience in that game was intentionally choosing that path and managing to succeed on the final mission after umpteen tries (you have a crappy ship and overwhelming odds), only to have the landing autopilot fly me into the side of the Tiger's Claw. RIP.
The most frustrating part was getting halfway through the campaign, only to discover that disk 10 was corrupt. I had to send away for a new one, which was a bit of a process because companies at the time were loathe to give additional physical media to avoid piracy. It took about 3 months to finally get the new disk.
Lol. I had the corrupt CD problem during my play through of "The Longest Journey". I appreciated the irony, as it added several months to the experience.
I played through original WC in the early 2000's, trying to win all missions. I got stuck on one that you really were meant to lose(escort, large numbers of attackers meant you had to execute with speedrun precision to have a chance) and stopped there. Later I looked more carefully at the walkthroughs and learned that the campaign progresses along the win path if you win most of the missions in the sector - you don't have to get 100% of them.
I always admired the series for its world-building sensibilities. It's simple stuff - Star Raiders had the essence of the gameplay in 1979 - but injected with a lot of atmosphere.
Even if you "win" that mission, you get the losing cutscene and the commander chews you out for not meeting your objectives even when you did and are put on the losing path - at least that's what happened in my copy of the game, so it wouldn't have been worth the effort.
I distinctly remember this in wc3 (the first one I played), because for a long time I thought the game was broken. I found out losing a mission didn't make you lose completely (a rare concept at the time) but didn't realize the next one would be harder. So I just got stuck there for months. Note that I was probably 9 years old at the time.
The most frustrating part was getting halfway through the campaign, only to discover that disk 10 was corrupt. I had to send away for a new one, which was a bit of a process because companies at the time were loathe to give additional physical media to avoid piracy. It took about 3 months to finally get the new disk.