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we are leaning towards a Weatherby Vanguard s2 in .223
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yes. Good choice
Take a hard look at Savage as well.
as for optics, I will admit I'm more into the "hunting style" scopes than the LR target or "tactical" variety. From my experience with them, I recommend a Burris Fullfield II or E1. Either the 3-9x50 or 4.5-14x42. I have always found Burris to be a scope comparable to other scopes that cost twice as much. Very clear, bright, and durable. When shooting paper, the more magnification the better IMO. If he ever plans on strecthing the range out past 200 yards, (he probably will) the 6.5-20x50 would be nice.
The Vortex Diamondback is also a very good scope for the money.
I'm sure there are other great scopes out there for you and your son's needs, I just haven't had experience with all of them