1) I doubt that changing the FD will affect crosschain rub. It's more a function of the bike's design and how well the FD is set up in the first place. But the Tourny stuff DOES look cheap, no matter how well it works, so feel free to replace it for cosmetic reasons. You live in the City; style is important
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2) I'm pretty sure all you have to change is the pad/pad holders to get the quick-change brake pad feature.
3) My pick for best bang for the buck on derailers is the older Shimano 500CX/LX. They look great, work better, and can be had cheap.
4) A chain with a quicklink-type link is MUCH easier to clean.
5) You want to spend money on a urban commuter, put the dough into bulletproof tires and tubes.
Just my 2 cent's worth, but you DID ask.......
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