I am currently driving a '97 5 speed Outback that I bought new, when I am not driving my "wife's" Prius. It has had a bunch of work in the last couple years (head gaskets, timing belt and pullies, water pump, accessory belts a year or so before, new battery wiring) and is still below 90K miles. I have done some mods over the years, Whiteline rear bar and front/rear links, short shifter and Cusco front stay bushings, 16" Impreza RS wheels and 2 1/4" catback exhaust. It went 6 months or so drip free after the head gasket work, but is dripping some oil from the right front now. No rust, nothing worse than some door dings, no holes in the upholstery or carpet. It is cheap to register and just passed an emissions test. That said, I have been driving it for 15 years, it isn't fast and AFAIK can't really get significantly faster without spending silly money.
I just drove a pretty nice '07 OBXT Limited 5 speed manual today, 55K miles, one owner, all or most records, good condition over all and an AZ car since new. It has a single door ding, some stains on the roll-out cover in the back, a hole in the carpet near the gas pedal and the cargo net on the back of the passenger seat is droopy. I drove it for 15 minutes or so, didn't get on the gas much. It drove fine, clutch pedal is stiffer than I expected but the owner said it has always been that way. It is a reasonable price, no sales tax since not a dealer and I wouldn't have to finance it. It was nicer in every way than mine (power everything, leather, giant sunroof, nearly 100 more hp), but I guess it didn't knock my socks off. If I were to buy it, I would immediately start looking for some LGT wagon springs and maybe front struts (for Konis) or the Bilsteins if I could find a decent deal.
I suppose I am practical to a fault, but I probably won't have to put any significant money into my old OB for years now as I don't usually drive it even 5K per year. I have a complete '04 STi takeoff suspension in my garage and also an '05 WRX wagon setup, both 20-25K total miles (bought the WRX first, then decided STi might be better). I have a line on some '04 STi housings that will bolt on and also have contacted a local welder who can weld up the lower holes on the '05 housings to move them if the '04s don't work out. I have the camber bolts and 3/8" saggy butt spacers that should make the STi stuff work great in back. Overall, I guess I don't hate my car, I am used to it and it is cheap to own.
I am also considering a WRX or STi hatchback or maybe even a VW Jetta TDI Sportwagon (all manual transmission). I have 4 dogs, 2 kids and am used to having plenty of hauling spacer. Would it be foolish to skip having the OBXT checked by a shop with single owner and records? What should I do?