That is a brute! The longest thing I have is a 300 f4 and that is plenty for what I tend to shoot. For street photography if you got the eyeball in focus that is about that would be! My favourite lens for "remote" street photography is an ancient 200 f4 Nikkor. Light to carry, easy and quick to focus and it looks great on full frame digital. I never liked it that much on film, but it really has come into its own in the digital realm.
I haven't had a whole lot of Leitz glass over the years, but had a 50 f2 Summicron with my M3 and have one each for the Leicaflex SL and SL-2. I've had a ton of great 50mm lenses over the years including Zeiss, Schneider, Nikkor etc. but the Summicron has a "look" all its own. It isn't just about contrast and sharpness, but rather how the lens handles the mid-tones.