haha found another street photog lover!
yes, DSLR is kinda hard for street shooting...I using Fujifilm X100, so is basically purist for street shooting
IIRC, the nifty 50mm is a bit slow as it does no using any USM focusing and very tight on street, a 28 or 35mm lens on APSC will do the job

but as other have said, there is no gear that define for which purpose, I use macro lens for portrait and even telephoto lens for landscape...

guess can have a shooting session together and pass you some street photog skills and experience, I normally scout around bukit bintang and petaling street area

some of my shots

P Balloon by Junrong LuLu, on Flickr

you can see me in action through his spec

Macha cool spec~ by Junrong LuLu, on Flickr


by Junrong LuLu, on Flickr