Hello Damian,

I can give you some advice on Question #2 for you:

Try a Campagnolo rear derailer with a Regina rear freewheel. Use either standard Campagnolo friction shifters, or either Shimano Light Action (for those on a budget who want Retrofriction) or Simplex Retrofriction levers.

If you must have indexed, I suggest you try some of the late Suntour 7-speed index equipment. They're considerably less fidgety and prone to wear then Shimano's current Hyperglide. It's also a tad easier to adapt them to an older roadbike that may already have, let's say, Suntour Cyclone.

Take care,

-Kurt