Crazy8: here is my 2 cents.
Q's
1) When it comes to rounds is it worth the money to get something like Winchester Ballistic Silvertips or am I just as well of saving some money and using Remington/other rounds?
For whitetail and black bear, if the good old Rem Core Lokts shoot good for you that is all you will need. The "premium" bullets do have advantages on bigger game like elk and the bigger bears but not for your purposes.
2) I know "grain" is a weight measurement but what is best practice with what to use? I know some people pick the medium grain so they still get a good speed and knock down power without sacrificing to much of either.
For the most part the bigger the game the heaviere the bullet. If I were you I would try bullets in the 150 - 180 grain range and see what shoot the best out of your rifle and sight in with them.
3) Are lower grain rounds better at one thing where higher might be better used on other things?
See 2 above
4) I know I should spend between $300-$500 on a good scope, any recommendations as far as brands or even specific models?
I have had excellent results with the Burris Fullfield II scopes with the BDC reticle.
5) Is it best to still stick with a 100yd zero when dialing in the scope or should it be zeroed in higher?
If you are not using a scope with a ballistic reticle, you should sight in about 2"-3" high at 100 yds. That would allow you to pretty much hold right on out to around 300 yds. (but you need to shoot at this distance to verify before shooting at game)