It's going to be tricky to tick all these boxes. If you want something that turns heads, that normally means a premium model such as a Porsche. In which case, you'd be expected to have anything but the most basic oil and filter it serviced at a specialist. Plus, if you're after mod cons like power steering, air-con, decent stereo (and soundproofing) then you're looking at cars that are a bit more complicated. If you're after something that's easy to get in and out of and doesn't have harsh ride, then you may have to think outside the box. You could go for something traditional such as a Triumph Stag (assuming you want to keep it Triumph), which is still very much a classic two-seater with a great engine. Alternatively, look at 911 ownership for a bit of wow-factor, and a decent compromise between mod cons and specialist servicing... and don't discount the later Jaguar XJ-S. We know plenty of people who own Honda S2000s and are terrifically happy with them - stunning performance and reliability (see also Nissan 350Z). Sightly left of centre coupe options to consider - BMW 8-Series and Mazda RX-7 or RX-8 if you're feeling brave, Toyota Supra. We'd also have a look at hot hatches - cars like the Mk1 Golf GTi and Peugeot 205 GTI are excellent to drive, have reasonably mod cons, and can be maintained at home... they also have plenty of wow-factor. Perhaps something like a TVR Griffith would also suit you.