Yes, I would say that it would be fairly normal for the numbers to be worn smooth, especially if the watch was primarily worn with a thcker leather band. However, if you were to get in very good light with a loupe you could probably make them out, but it might be very difficult. Yes, the bracelets can be dated, sort of by the clasp. Generally they will be engraved on the folding pieces. They may say C&I Rolex USA with a two part date like 7-62 indicating July of 1962. Those are USA made bands...there are Swiss ones too and they have similar markings but they will say Swiss Made or Suisse and also have a date engraved.
Sure, it would be nice to have a 1964 steel and 14k bracelet for your watch...whether it makes that much difference...I doubt it. If you had a triple date moonphase from the 50's or something like that...sure. On a 1005 not that big of a deal. These bracelets stretched and were replaced just like a worn out part on your car. If you come across a nice one that is engraved 64 and you have the money...go for it. If not find something that works for you and enjoy the watch.

best,