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First big question is what type of bear do you plan on hunting and what type of bears will be in the area? If the answer is only black bear, you will be fine with the .300. I think a .30-06 would work just fine on black bears. If the answer to either question includes the word grizzly in it, I think I would go with the .338 in a Remington Ultra Magnum at the minimum and possibly think about getting something in .375 or .416 Rigby. Of course, the .375 and .416 Rigby aren't available in a lot of entry level rifles. A .338 Lapua might not be a bad cartridge, but I don't know of any entry level rifles chambered in it.
Remington offers the Model 700 XCR in .375 H&H and .375 Ultra Magnum, but the MSRP is around $980. Usually you can get the rifle for a decent amount below MSRP.
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The pond, waterfowl, and yellow labs...it don't get any better.
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