Working Designs was the best localization we could get at the time, and there is a reason why we remember them fondly, although I definitely much prefer the unworked versions of the games, as a lot of the gameplay changes didn't age well. The idea at the time in the US Market was that if someone could beat a game in the duration of a rental, they wouldn't then go out and buy it.
WD was
not the best back then. That's a myth their fanbase spreads to justify their faults. There were plenty of perfectly fine translations from other companies. Was the grammar perfect? Not always, and that's the one thing WD did right consistently. (It's easier to do that when you only publish on systems with the technical ability to avoid old-school character limits.) But there was a serious effort to translate as accurately as possible within the limitations of the structure of the companies and the platforms they were on.
Ted Woosley actually put as much effort as he could working on a system not made for long English texts. And the various translators who weren't allowed to see the game itself nonetheless never threw out the script to write dumb jokes and rewrites.
WD's approach was objectively bad translation. Their method was to write down the basic plot, throw out the dialog, and replace it with whatever they wanted. Entire characters were warped into someone else. (See "Boner" from
Alundra, whose entire character and dialog was changed to one lame joke about how much his character art looks like Spicoli from
Fast Times at Ridgemont High.) Jokes were inserted into serious moments and other places where there wasn't any such thing, deflating tension like in the worst Marvel films and taking the player out of the experience.
And then there's the socio-political stuff. The pop culture jokes were not the only products of their time. Dated Clinton-era references not only looked like Jay Leno D-material, but pushed a political perspective on something completely apolitical. Regardless of your views, alienating ~50% of the audience for no reason other than "huh huh, I heard a funny one at the water cooler" is a dumb business move, let alone measurably bad translation.
And then there's the bigotry. The ebonics joke from
Albert Odyssey is the most notorious, but there's more subtle ones in
Lunar and other releases that you can notice if you use decent reading comprehension. And there's also
less subtle ones, like how
Popful Mail repeatedly used the R-word and blatantly used a racial slur that you'd think died 100 years ago.
Don't get me wrong, I'm glad we got these games in some way. But it is possible that we might have got them without Vic Ireland's grime all over them; in fact, it's commonly believed that we don't get rereleases of WD games that often because Vic won't allow them without his approval and control. (Note that he insisted on firing the majority of the original voice cast as a condition for the PSP
Lunar to be made.)
In fact, the fanslating community probably would have got to them by now if not for the existence of ① already existing "good enough" translations causing inertia and ② a fanbase that rabidly insists they are not simply good enough, but
absolutely perfect. In all likelihood, that's also why we don't have a translation for
Lunar Magical School either. Do it right, and you'll be told you ruined it based on the "totally Knee Hung Hoe Joe's Shoe" crowd's understanding of what it's "supposed to be"; do it wrong, and you'll be patted on the back by people who aren't even fans of
Lunar, but fans of Vic Ireland — which would not be rewarding, to say the least.
In reality, we got just as much screwed over by WD as we got rewarded. The games were fun, and we got to play them before emulation and rom hacking made JP-only games easily available, but in the long run we've lost out on what could have been the true experience of playing these games as the creators' intended. I'd have rather got a "bad" translation of the Ted Woosley variety than what WD gave us. At the very least, some fanslator would come along eventually and fix the mistakes.