What I bought
Chrysler 300M Special
Woulda... if it wasn't for a cracked head

I get a bit sad every time I see one on the road
Cadillac STS
Coulda...
Lincoln LS V8
or
P71 Crown Vic (original car I looked at purchasing)
Shoulda...
Honda Civic (or some other small fuel efficient car)
What I think now...
I
really wanted the STS. If it wasn't for a cracked head the dealer mechanic caught while we were signing the final papers on the car, I'd be driving it right now.
I never really looked at the Lincoln LS V8 until after I had bought the 300M, but had I researched a tad more before purchasing, the LS V8 would have been a bigger contender.
I'm glad I didn't get a P71. Yeah they are cool, and people GTFO of your way when you drive one, but it's hard to find one that isn't worn to hell.
I should have gotten a small 4 cyl fuel efficient car. I wouldn't be as worried about it getting scratched or dirty, and it would be a lot easier on the wallet when at the pump.
Overall, I am very happy with the 300M. It's surprisingly quick for it's size, it's actually a bit quicker than the STS, and a little quicker than the P71...a little slower than the LS V8 though. It sounds badass, and the interior is excellent. It's not the most fuel efficient car, but it's not too bad either. It gets around 16mpg city and up to 26mpg on the highway. With mixed highway/city driving, average MPG sits around 20/21.