The one issue is if this is one driveway that is shared by both units. That's the way it is in my duplex--there is one driveway, a little more than one car wide, that leads to the back of the house and parking for all the cars.
There's no way, really, to shovel half the driveway and have a clear path to the street. You'd either shovel the left half of the driveway, or the right half, or the half near the street or the half in the back of the house, but no matter what, shoving half would mean that half the driveway would have snow on it. And when cars drive over that snow, as mentioned by several PPs, the snow gets packed down and is much harder to clear off the driveway.
So Tom may just want a driveway that doesn't have packed snow on it. And the only way to get that is to shovel before cars drive on it and before too many people walk on it. Waiting until everyone has left for work and then come home after work simply doesn't cut it--there will be packed snow and the chance of "ice ruts" is high.
If that's the case, I like the suggestion above about trading yardwork. Tom shovels the driveway all winter by himself, but in return, the OP and her boyfriend mow the lawn or weed the flower beds or something, so that Tom doesn't have to.
I'm curious. Was the OP's boyfriend living in the duplex before the OP moved in? What was the shoveling arrangement then?