As an entry level, you can't go wrong with .270, .308, or 30-06. I prefer a Winchester Model 70 (out of production but you can still buy them) or a Ruger Model 77 bolt action. Simple, reliable, and accurate. Any of those three rounds will be plenty versatile. I prefer the 30 caliber rifles for the variety of bullets available. The 168 grain bullet is good all around, but you can go lighter, maybe 130 grain, for varmints, and up to 200 grain for mule deer or even moose or elk, IF you get close.
Also, these days Savage makes a couple of nice rifles, their Model 110 is a very good piece. Mossberg has their 4x4 bolt action, it too is a very nice and very accurate rifle. They are both a little more affordable than the Winchester or the Ruger, but still VERY solid, and accurate as well.
Get a scope, either 3x9x50 or 4x12x50. A Simmons will be more than good enough for an entry level rifle/scope combination. If you spend too much money on a scope, you'll not have enough money left over for a good case (I like a hard case AND a soft case, I use the hard case to store the rifle, but the soft case makes it easier to transport for hunting) and plenty of ammunition. You can get a Leupold or a Nikon, but you'll spend a lot more for it, enough to hurt your budget. Don't get me wrong, they are GREAT scopes, but they are twice what a Simmons costs.
I recently bought a Winchester Model 70 300 Winchester Magnum with a 26" barrel and a Simmons 3x9x40 scope, on
http://www.gunbroker.com, for a total of $425 including shipping and transfer fee. It was new in the box. I have found that the 300 Winchester Magnum is about the best all around commercially available round there is. However, it is not really an entry level round, the recoil and muzzle blast are a bit much for the uninitiated. I've owned several 300 Winchester Magnum rifles, and never once have I had a barrel warp, I haven't even shot one out. And I shoot often, with very powerful handloaded ammunition.
You'll find that a GOOD quality wood stock will add well over $100 (at the very least) to the cost of a new rifle, IF you can find one. I love a good walnut stock as well as anyone, but I carry and shoot my rifles often, and I understand the advantages of synthetic stocks. For a rifle you'll SHOOT, a matte finish with a synthetic stock is really the way to go.
If you can find a friendly dealer who will handle the transfer for you for a decent fee, you can go to
http://www.gunbroker.com or
http://www.auctionarms.com and get a good deal, so long as you know how to work an auction, like you would on ebay. I've bought several nice weapons that way, the local shop does the transfers for a flat $40.
As to reloading, I couldn't afford to shoot my toys if I didn't reload, but it is NOT a hobby for everyone. The average cost of an RCBS reloading kit is over $200 these days, although a "Partner" kit is plenty good at $160 or so plus dies and a shell holder. Dies and a shell holder will cost around $45. Powder is usually $18 for a 1 pound can, primers are $15 for a brick of 1000, and bullets are around $18 for a box of 100. It is the best way to get accurate powerful ammunition you can afford.