Unless i knew without doubt the history of a 14 year old hoonbox i wouldn't even consider it. I've got one old wrx I've got my eye on, but i doubt strongly the owner will ever come up off of it. If he does, then it's more of a trophy and a driveway ornament.
I just bought a 06 STI and previously owned a 11 WRX. Equally fast on the street - WRX was more refined and I had more confidence that it wasn’t going to break. Probably psychological but I’m happier with the STI because it is “top of the line” and the transmission freela nicer. Neither car is currrently (or ever was to my knowledge) significantly modified.
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The common sense answer is to, as stated, buy the most recent car that you can afford.
That said...sometimes there are certain cars that are subjectively "special". The '04-'05 STi was a GD (so awesome to me, they really just don't make raw cars like that, anymore, that I've seen), had that unequal-length headers boxer rumble, etc. Finding one that hasn't been thrashed is, of course, a problem.