At least you have a driveway to park it! Have you thought about covering it during the winter?

It's in storage now, and covered.

Would it be a bad practice to not level the front tire when your TT is on your driveway?

I think it depends upon how long you plan to park it. For overnight before a trip it probably isn't a big deal, but for an extended period I'd be more comfortable bringing them level. But that's just me.