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?

I would just try out some different brands, as many others have already said. That is sound advice and you can take it to th bank.

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.

I only use 150 in my 30-06. Anything bigger is just slower and has more recoil. Maybe go 165 for bear. I 150gr corelok will put a large hole in a whitetail.

3) Are lower grain rounds better at one thing where higher might be better used on other things?

In a word, YES. Bigger animal = bigger bullets.

4) I know I should spend between $300-$500 on a good scope, any recommendations as far as brands or even specific models?

You're right on that one. Good optics are everything. I have always used Leupold and Nikon with excellent results. The Leupold VX-III scopes are hard to beat and Nikon Monarchs are crystal clear and very ruged also. Burris also makes a nice scope but I don't have much time on one.

5) Is it best to still stick with a 100yd zero when dialing in the scope or should it be zeroed in higher?

Alot of people go 1", 2" or even 3" high a 100yds. If you are hunting in places where you may need to shoot out to 3-400yds frequently then thats all well and good, but for a 30-06 and shots inside 200 yds and the occasional 300yd shot., I like to sight in 1'-1 1/2" high a 100yds. Thats will put you dead on at 50yds and 150yds and maybe 3-4" low at 200yds. I don't like dealing with that high arching line of sight when I may have to take shots at moving animals or tight windows. Just my opinion. You can look at some ballistic charts to get some ideas about your bullet drop and such.