Porsche Boxster
When the Boxster hit the roads in the mid-1990s, traditional Porsche enthusiasts questioned the logic of the car. There was no market for an affordable entry-level Porsche at the time. The Boxster was different than the Porsche models on the market before, but the car became a success. The Boxster was a well-designed car from the ground up and still manages to keep that reputation going today (via Motor Trend).
The Boxster has a very affordable resale value, which means anyone can afford to pick one of these cars up. Another great thing about the Boxster is that the styling is timeless, even if you drive one today, it still turns heads. The Boxster was one of the most affordable and cheap to maintain Porsche models built.