For the money, you just really, really can't beat a late 80s Trek. They are just great riding, light, attractive (and still made in the USA) lovely steel bikes. This 1988 Trek 360 that I fixed up for a friend has a nice Suntour 12-speed setup with indexed shifting. I swapped out the bars/levers for something a little more upright. Eric, if you're reading this, I take back the aspersions I cast at the Sturmey Archer brake levers, they look very nice and are terrific levers to boot. Thanks!
This bike was gotten for a mere $230 in gorgeous perject working order and after another hundred-ish dollars in persnickety parts swapping, it's a fleet 21 lb. city bike. What does $350 get you new these days? A decent saddle and a set of cheaper STI levers maybe. Certainly not much of a whole bicycle.