> > So far, all I've done is the trainer. Should I play the games in increasing order of difficulty, or does it actually matter if I play them in the order it shows?
>
> It doesn't matter which order you play them in, but I recommend you save Outlaws, TOA, and POA for last. I think you should play Brackley Hall first, as it makes the other games a little easier. You won't catch a lot of the humor in FQ2 if you play FQ2 before finishing FQ1.
>
> Otherwise, go any order you'd like. I beat GOA before I started FQ, and it made FQ a snap.

I generally agree with the above. My thoughts on the subject are:
1. The Trainer should be played first, if only because it takes just a few minutes and you learn a certain valuable lesson about persistence in AGL games.
2. Most importantly, FQ should be played before FQ2, because, played first, FQ2 will just seem wacky. It's meant to played when you know a lot about the "history" of the place and can put the humor in the right context. Also, since FQ2 refers to actions "you" have done in FQ, FQ2 can spoil some of FQ.
3. In terms of plot enjoyment, it's probably a bit better to play POAT before OAT (PoA and ToA for some of you) because POAT stands on its own, but OAT builds off that a bit, making references to some things from POAT. (In the future, I think the release date ordering will continue to hold -- POAT, OAT, FAF, and finally SOAT would be a good order to play them).
4. In terms of difficulty, it might be best to take them approximately from easiest to hardest, if only so you don't get hopelessly stuck in one of the hard games and think they're all going to be like that. Whether that should outweigh the previous consideration, I don't know.