Since you live in the chicagoland area, I'd like to first invite you to the regional forum and in particular the fairly active chicagoland chat thread. Alot of good guys with alot of knowledge and local connections.
Regarding the cars, alot depends on your wants/needs/$. I don't think that you can go particularly wrong with either unless your needs don't suit the car.
I too bought an 07 e90 335i with no sport package etc. I had my reasons though...kids, dd, probably not going to see the track for awhile, knew I had $ to burn on mods anyway.
In the end, I got a the bmw perf front bumper and skirts, wheels and coilovers to offset the lack of sport package. To this point, I have not missed the sport package or oil cooler at all. My only disappointment is the fact that I cannot install the bmw perf seats I want without issues.
I will be getting an oil cooler that is twice the stock one this year because I want to upgrade my tune.
Again, it all depends on your situation.
Ihsanshaik - X/Vasillalov - X/Nood1es - X/Countless more I can't recall - X