Fun, comfortable car for long term ownership (5+ years)

If long-term reliability is a primary goal, I would suggest taking a look at the 2004-2008 Acura TSX and TL. If you want a manual transmission, the TSX will be your best bet. The TL with manual is very hard to find.

The TL is a great car with lots of power even with the auttomatic, though. But the TSX is a lot of fun to drive with the manual!

I'd be wary of buying an older vehicle with a navigation system. You'd be amazed how outdated a 2007 or 2008 nav system is today. And if the HVAC and audio controls are integrated into the nav screen and something breaks, the repair cost can be astronomical!

Once just about any German car has over 100,000 miles expensive repairs are a significant possibility, if not guaranteed. The best candidate for any such car is someone willing and able to do nearly all of their own repairs. There's no such thing as a cheap Audi or BMW; the prices of older ones are under $10k for a reason.

The Acura TSX is a good suggestion if you're okay with front-wheel-drive and don't need a lot of power. They also offered the 2009 and up TSX with a V6, but with this engine it didn't handle well. The first-gen cars (2004-2008) are the most fun.

Among rear-wheel drive sport sedans, the Infiniti G37 probably has the best combination of reliability, performance, and a reasonable price.

The Lexus IS might be another possibility, but it's less fun, less roomy, and more expensive than the Infiniti. Plus no manual transmission with a sufficiently powerful engine. Higher prices probably reflect that it is the best bet for ultra-long-term reliability, though.

The Acura TL can be fun with a manual and SH-AWD, but it's larger and less agile than the others discussed here.