Should be killer! That's what I did as well, stripped, sanded, stained, oiled. Oil inside should be fine, especially if you aren't concerned about preserving a sound. The difference likely isn't massive anyway. I noticed just a warmer, thumpier, sound, HOWEVER, that was after removing the wrap as well, so I never had a true before/after with the oil, did it all at once. I wouldn't worry about it.
Bearing edges always sound best when they're as sharp as possible. The sharper, the more attack and resonance you'll get. The rounder they are, the less attack, and less sustain you'll get. If there are any nicks or flat spots, that can screw up tuning, and give you odd resonances/buzzes in your head once tuned up. If you don't sand the bearing edges and just apply a bit of oil, that should be OK, but just don't knock down the edges at all if possible. Some guys actually wax the bearing edges to get a more consistent tack between head/edge. I did it, but again, since I did so many things at once, I can't say what it did by itself for tone.
Mounting technique is a big deal too. shell-mounts hinder sustain much more than rim-clamp mounts. I personally use a snare stand for my tom, but I only use one rack tom, and one floor tom.