- what's it mean that "it's going to live outside ..."? meaning, overnight on the street in the rain? not a good idea for any bike.
- i like the sram pc830 chain. i put it on all new builds. it goes for less than $15 shipped on ebay.
- definitely install a rear brake unless your bike is a fixed gear. you need a backup. this actually saved me recently when a front cable i had worked on the night before slipped through its anchor. it only needs to fail once for this kind of thing to leave a lasting impression.
- count the chainring teeth to determine diameter. there's a formula for estimating bcd -- see sheldon brown on that. 144bcd is a popular size for the vintage, but your small ring will be limited to 42t, no smaller (for all practical purposes).
- if replacing the cottered with a cotterless, i'd let your lbs remove or loosen the cotter pin and crank, and you can do the rest probably with the cheap $15 park spanner wrench and an adjustable wrench.
- happy riding. i bet it's a lot of fun riding in nyc...