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You first have to decide if you want a true roadster or some "sporty" coupe in convertible form.
If you want a true roadster under 30K new, there's only one I'm aware of and that's the Mazda Miata MX-5. The Miata is a true driver's car and there are millions of devoted fans out there.
The only other option is the Honda S2000 (about 32-36K new), but they stopped making them in July 09. New ones still sell north of 30K if there are any on the showroom floors for sale.
I do have one, and it is a very comfortable, quick roadster. It isn't a 1/4 mile car, it's a momentum car, so if you like the torque-heavy V8s and V6s, you may not like the S2K (or the Miata). It is a car you should know well before you drive it hard. The power comes on very high in the RPM range, and that also bothers some people. If you want to buy used, I would choose a 2005 or later with low miles and one adult owner. Good ones can be had for 20-22K. Mine had a little under 8K on it when I purchased it -- pretty much a brand new car for much less than new, MSRP. I spent a few months waiting for the right one to show up and purchased it about 10 minutes after the listing went online :-)
The true roadsters in the "upper middle" price range when new, like the BMW Z4 and Porsche Boxster can be had around 30K used (some even lower), but the price/performance/upkeep issues would lead me to buy a new one or not have one at all. If you're pushing yourself to the edge of the price point to get a used car, you run the risk of costly repair making you hate the car (new brakes and higher mile routine service costs on these cars can be high).
If you just want a convertible, there are many choices out there. I'm not familiar with any of them personally. I don't think I'd ever purchase one, but I'm sure they are fine cars.
(Edit: I didn't forget the Saturn and Pontiac Roadsters. I just don't think they're worthy of mention. I assume both product lines are gone or out of business or whatever. I guess one could be had used, but from my conversations with owners and what I've read about them, they just didn't get it right with those cars. I suppose a GM fan would love the turbo charged version for the engine and appearance. They were both a flash in the pan, IMHO.)
My father bought one of the Mitsubishi 3000GT VR4s when they first came out because he thought they were very comfy. He's 6'4". I'm 5'3" (or was at that time) and thought they were terribly uncomfy.
Mazda Miata. If you want economic performance, shop for the MazdaSpeed Miata. I think Mazda has official Mazda performance parts for the Miata to make it faster. If you have your heart set on the Porche, consider skipping the traditional 911 and go down to either the Boxster or Cayman.
and they are easy to mod to have even more fun. I just had a ride in one with near 500hp, it would put quite the surprise on many vettes and porsches for less $$
Either a Miata or a 'vette would provide an exellent driving experience, the top goes down, the Miata is probably the more practical of the 2 - but you can definitely own a good older 'vette for a few years and not lose any money on it -
I have to agree that your budget is over-generous, you can find a good Miata for $15K or less, and I don't mean a beater either.
I would 2nd the Honda S2000. It's a lot of fun and loves to be revved high. It only comes with a 6-speed stick-shift, but it's a joy to shift - maybe the best shifter on the market. The Miata is more tame, but a solid choice and great value.
I would also mention the Mazda RX8. It's pretty unique and would fit your bill. It's got rear-swinging half doors adding much practicality for an every-day driver. It can't be had as a convertable, though.
The OP said he is partial to Porsches. He has $30K to spend.
I don't see why he doesn't just buy a Boxter. Or a 911 Targa.
A C6 Vette would likely have the most performance for the money.
I think the Sky is a terrible choice. Poor overall quality, a dealer network going to pieces, and an attention-grabbing but gaudy look. The Solstice is even less desirable.
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