Actually, it's prudent in my opinion to pick a spot where you have a good field of fire and let the does or naturally occuring feed/forage lure the buck out in the open where you have a clear shot. That is unless you can set up by a well used game trail in the thick stuff knowing bucks are using that trail regularly.
To illustrate my point, my blind is situated in intermediate cover- big trees and very little brush between an open field and thick cover. If I sit still, the deer will generally take their time between the thick stuff and the open field. However, seeing that while the does will walk right by make taking their own time, the bucks will come in behind me and decline my invitation- calls and scent lure- to circle around. Because of this, about two weeks into open firearms season, I'll be pulling back about 100yds across the open field to another blind and be downwind of everything. From there, it'll be probably 140yds to the thick stuff. I've observed bucks- some pretty nice ones too- taking their time across that field when they didn't know I was there. So, "playing sniper" should work out well in the scenario I'm setting up.
As to bullet weight, everybody has a preference. I know in my own case, I can put three rounds of Remington greenbox 150grain .30-30 in a 5" circle at 100yds with room to spare. If I were dealing with bigger deer, I'd probably be thinking of a bigger caliber in that same '94, like maybe .375Winchester.
As for "charging after the deer" after firing the first shot, all that is to me is giving the deer an adrenaline dump. It ain't a clean kill and it ain't gonna taste good. Nope, I figure the best course of action is to pick an upper-lung/spinal shot. It'll drop the buck in it's tracks and fill the lungs up with blood and death occurs pretty fast- usually in about 45seconds from what I understand. Personally, I'd rather the deer never knew what hit it.