Infinity M35x Bmw 750 series Mercedes Sl550 Lexus Ls460 Jaguar S-type 2000-2002 Some cars I might consider , when I am buying a car also.
Then I would suggest either the RX-8 which has 4 seats but really you can only fit 3 depending on your height. Its much lighter than the 350Z and if im not mistaken its not to much slower. The Lotus Espirit is a pretty nice looking car as well as im pretty sure its fast, the only down side is that you sit very low to the ground. Also the Pontiac Solstice GXP is a nice sports car.
Me personaly, I'd go for a car that I know has a good overall engine and a good built and then do body work. I've probably owned 20 cars over the past few years and the best engine I ever, I mean EVER, sat behind was a 1990 Oldsmobile Cutlass Sierra. It was an amazing piece of machinery.
Get a good stable car, all of these high end expensive cars, are just going to wear down your pocket, no matter how rich you are. Insurance will be insanely high, any damage, and insurance will rise even more, then if anything happens and is needed to be replaced, you have to go through that company itself, costing even MORE money. I would look through the consumer reports and look for one of the best rated cars altogether, instead of wasting your time reading dream cars from 12-13 year olds on an internet forum. I would listen to the people who deal with cars their entire lives, for instance, ask around at your local mechanic shop, ask what type of car is hardly ever seen due to their maintenance being so low in demand, ask which cars would be the number one choice overall. Wasting money, no matter how rich you are, will only ruin the fortune that you currently have. Spend money wisely, and not like some 16 year old girl who got her first paycheck and spent it all on shoes, then wonders why she can't buy dinner. That's just my 2 cents.
well i personally think sports car should be stick shifts, but seeing as youre in chicago, youd have to be shifting a lot and im not sure it would really be worth it. to tell the truth, i think for now, a pontiac solstice would be great. theyre cool little cars, they look nice and have really good performance considering theyre really cheap compared to everything else in their performance range. by doing that, you could invest the rest of the money and if its really very much, the returns could earn you enough to keep you living pretty good for a long time if you save enough of it