I would go check out some new guns at different costs and see what feels\looks best to you. Then if you like the guns that are more then 500$, I'd start looking for a used gun in that model. Either at a gunshop or local paper, even a gun show would bea good place to start. I'd wait until after this deer season to purchase. I've seen a lot of great deals on used guns after the season.

Id prob go with a popular caliber since the ammo is cheaper and easier to obtain. 243, 308,7mm-08, 25-06, 270, 30-06 something like that.

If you like the less expensive Savages then grab one of those with the lower end(of quality)scopes these guys mentioned and you'll be fine. Make sure you dry fire the gun to see what the trigger is like, some of the cheaper guns have horrible trigger pulls. The older and non-accutrigger Savageshave very heavy pulls for the most part. The Rem 7600 pump is a reasonably priced gun that shoots plenty accurate for deer and will have a feel you're more used to coming from shotgun hunting. You can usually pick one of them up used for 300-350$.

If any of your buds haverifle's try to see if they will let you try them out to see what you do and dont like. The more posts you read here the more confusing it gets sometimes. Most of the guns\calibers in question on the site are all personal preference. You just need some experience to know what you like or not.

Lastly if you are mainly doing hardwood hunting(usualy less then 150yards shooting)then don't overlook a good ol' 30-30. I think you can buy a new Marlin for about 350ish$ or so and then have some bucks to grab a nice fixed power 4X scope. The used Marlins are pretty common, you won't have any problem getting of those for cheap if you want to go that way.