As I remember from my bad box days, a smooth wine (if you can imagine, kind of like the sound of an electric car) is how a tip top first gear should sound. When it begins to sound like an old roller coaster, cranking and clunking up a hill, with each grind threatening to pop the gear out, you'll know the gear is on its way out.
However, from my experience, these boxes can last pretty good, even when completely shot and with no oil. You only really need to worry about the gears when it keeps popping out, even then, you may want to check the adjustment/calibration of the gear selector (two bolts on tunnel where box is mounted) before condemning the box to the bin.
As as previously mentioned, make sure you have the right amount of correct oil in the box.
Dom