The price makes it a pretty attractive proposition. I mean... its as cheap or cheaper than his new Mazda 3i.
And if it blows the engine? You can probably still salvage or part it out and walk away with at least $6k. Sure it would be expensive then, but not a whole hell of a lot more than a...
You can get a 996 in good condition for mid-20s. Then sell it for $10k in 5-8 years. Not a bad way to spend $15k.
Just be wary of the infamous IMS bearing problem and RMS issues. Otherwise they're supposedly pretty reliable.
FWIW I love the fried egg headlights, and never hated the 996...
My dad used to have a Legacy. He loved it, gave it to my brother when he moved out to California. Its still a great car, even though it had the obligatory Subaru head gasket failure. Actually, that's all that has gone wrong on that car in about 140k.