2006 Mazda MX-5 Miata Sport 2dr Convertible (2.0L 4cyl 6M)
This is actually my second Miata (I had a 2003) and while I loved the 2nd generation, the improvements to the third are fantastic. The car is just a blast to drive - feels much more rigid and refined than the 2nd-gen, while maintaining the car's signature dynamics. The additional room (I'm 6'1") was more than welcome, and more power is always a good thing as well. It splits commuting duty with a motorcycle - and is as close an equivalent to a four-wheel bike as you're going to find for this price. It is just impossible to have a bad day behind the wheel. Do NOT test drive unless you are completely prepared to buy, because there's a really good chance after a spin you'll be signing papers.
There's probably not enough room here. Power (and sound), handling, trunk large enough for a week's worth of groceries, tremendous grin factor.
Not much - I wish the center console cupholders were deeper for storage (I do my coffee at home). The cover intrudes to where it's not deep enough for a garage door opener. The door holder does sunglass duty. The car rides pretty high in stock form - MAZDASPEED springs will correct this shortly.