Thanks for all your info guys. It really helped out a lot. The first gear start is not really my number 1 priority, it's just something nice to have I guess. Last night, this broker told me that his '92 starts in second gear :-). We'll if he's not lying then it probably had an older transmission installed (thanks to you guys). So far, I'm going to look at an 87 300E with 187K mi for $3500(it has a 2" crack on the windshield), an 87 300E with a 2.6 engine and 200K mi for $4K, and lastly, I'm going to check out this guy with a 92 and a second gear start for $8k(really questionable to me).
Right now I think the harder choice is between the two engine sizes (2.6 vice 3.0). I have a 190E with the 2.6 engine and I'm happy with off-the-line acceleration, but then again, the 300E is a much heavier and loaded car.