Audi TT
The Audi TT was one of the longest-running two-door sports cars in the automotive industry. When the TT was released in 1999 the design of the car was groundbreaking. But that design remained the same for almost two decades with very minimal changes (via Readers Digest).

The maintenance costs associated with owning an Audi TT are some of the most expensive that you’ll pay. The car had to be maintained by specialty technicians, and those are difficult to find. There were other sports cars from the same era that offered the same amount of performance with fewer headaches.