Big Boy,
A couple of suggestions for you. I don't know how much experience you have with rifles. If you know some hunters with rifles of different calibers, it might be worth your while to ask them to shoot them to see what you like. Also, do you plan for one rifle purchase to cover most all hunting needs, or do you plan to purchase other rifles for hunting and form a rifle "battery" of sorts?
What terrain will you likely be hunting in? For instance, a 25-06 or .270 or even a 7mm mag would be good choices for wide open spaces where long shots are the norm. A short action cartridge such as .243, .260, 7mm-08, 308 would be nice to have in a lighter rifle if you hike alot in the mountains. A 30-30 works great for woods hunting and is probably the least expensive option for both rifle and ammo.
What other animals do you envision hunting in the future? For deer and varmints/predators, a .243 or maybe 25-06, or possibly a .270 might be a god choice. On the high end, such as for deer and maybe elk in the future, I'd get a 30-06 or 7mm mag, or maybe a 308. For deer and black bear, I'd probably advise something like a .270, 308 or 7mm-08.
How important is ammo cost and availability. The least expensive medium/big game cartridges are 30-30 (cheapest), then 30-06, .270, 308, .243 (which are all about the same cost). The cheapest varmint/predator cartridge is .223. These cartridges are also the easiest to find generally. Do you plan to reload? If so, you might consider excellent deer cartridges such as the .257 Roberts, 6.5x55 Swede, .260, 7x57, etc.
IMO, the sweat spot for deer hunting is cartridges between .25 and .28/7mm caliber (non-magnum) and the 30-30.
The bottom line is that good choices for an all around medium/big game rifle include the 30-06, .270 and 308. One of those is probably the best choice.