It's hard to convince a Porsche lover to make the switch to another brand.
This. If you want a Porsche, get a Porsche. This isn't supposed to be a rationale purchase -- buy whatever makes your heart beat a little bit faster and makes you turn around to check it out after your park it.
As others have mentioned, the 996 was definitely a bit unloved, and prices reflected that. But that's changing, and prices on clean examples seem to be going up. The 996 Turbo used to be a smoking deal, but prices on those have gone up 50% in the past few years.
I think the 996 is a great 911. While it definitely lacks some of the heart and soul of the previous air-cooled versions, it's a more civilized car than the previous models. It's a bit more of a Grand Touring car than the earlier models -- it's very comfortable for putting in some serious miles.
As others have mentioned, the IMS bearing is an issue, but you'll find a lot of the cars have already had that addressed at this point. It's not an inexpensive car to maintain, but if you can do a few things on your own (oil changes, etc.), it's really not that bad. I like the 6-speed coupes, but there always seems to be a ton of Tiptronic cabriolets on the market, so the prices actually go down with these cars if the top goes down.
You can get a newer Boxster S in your price range. Smaller cars, but a lot of fun. They feel more like an earlier 911. They also have the IMS issues (86 Boxster). I haven't owned or driven a Cayman yet, but they're basically a Boxster coupe, and a Cayman S would definitely fit the bill (although you probably won't find one under $25k).
By the way, I've had very good luck buying Porsches from PCA members. They obviously tend to be enthusiasts, maintain their cars well, and don't look at you with a blank stare when you ask about the IMS . . .
Lastly, another really great GT is the Jaguar XJR. Supercharged V8 coupes & convertibles that are absolutely lovely -- especially the coupes. Aim for a 2003-2006 XJR which has the 4.2 supercharged V8 mated to a ZF six-speed transmission. You can pick one of these up for way under $25k. British flair with Ford reliability. Certainly much softer than a Porsche; again, more of a high-speed GT car than a true canyon carver.