Choices, choices...
Weatherby is nice, I love the way it fits my cheek, but they were always too costly. I just saw a nice fluted barreled synthetic stocked variant in 7mm Weatherby Mag Mark V used for ~$500. If it was in .30-06, it would have been mine. Real Weatherby magnum ammo is expensive and not always in stock.
Winchesters are nice. The pre-64 Model 70's are classics in the truest meaning of the word. I like them for their feel (when guns were walnut and blued steel) not necessarily the controlled feed.
Post-64 Winchesters and Remington 700's are a tossup. I like the new Winchester Classics, but for deer or black bear hunting do not see an advantage to the controlled feed. I personally go Remington 700 and have 3 (.30-06 BDL, .308 PSS, .223 LTR). The triggers are highly adjustable if you are reasonable with pull weight and competent. All mine are factory stock except for torqued action screws and are MOA or better rifles with the right factory load, with the PSS being much, much better than MOA. A used 700 ADL with blind magazine can be had for under $350, although I would get a BDL with hinged floorplate. Avoid the DM (detachable magazine) models as they have had some feeding problems.
For bang for the buck, used Remington 700 (especially the long action ones as the short actions are scooped up for various varmint/tactical projects. (Leaves a lot of spare $$$ for the scope.) Then the Winchester. Finally the Weatherby. That said, I have never met an unhappy Weatherby owner so take your choice.