Just my opinion.....I am doing the same as you, looking for a new rifle, and have thought about it a lot. I am seriously considering a 30-06. My reasons are; You can buy ammo for it almost anywhere ammo is sold and you can find a load that will handle any animal in North America, from varmints to bears or moose. I really like the Remington 700 also, but because of its afffordability I am looking at the new Marlin XL-7(@$350).  Hope this helps you in some way. Godspeed!

I have many rifles in many calibers but the one that always finds it's way to the stand with me is my Browning A-Bolt Composite Stalker in .270.  I bought it at Academy 7 or  8 years ago for about $400.  They've gone up a little since but not much.  This rifle is topped with a Leupold VX-II 3-9x40 ($300).  It shoots under 1" groups at 100 yards (sub-moa).  It's not a pretty rifle but damn it shoots good. 

Now, since you're asking us to spend your money, you may want to consider a true heirloom to leave your son.  Something like an original pre-'64 Winchester Model 70 in .270.  Or a Weatherby Mark V (German made) or older Sako Finnbear.  Perhaps a truely collectible rifle like you'd find in Cabela's Gun Library.  If you really want to get personal, you could have a custom rifle built on a Mauser action.  Expect to pay $2,000 or so.  No doubt that it would be very collectible though.

Best of luck and let us know what you decide.   

go to a gunshop and look at the thompson/center encore.  if that is to expensive, look at the cva, and now i see knight making the guns with enterchangable barrels.  i got a thompson this spring and have a .243, 30.06, and muzzleloader barrel for it.  you can get a 22 for it also.  this way you just get a barrel for whatever you are gonna hunt.  my next barrel is gonna be a shotgun for turkey season. 

right now academy has a the marlin xl7 for $279.  i was seriously eyeing it for a cheaper gun for the time being.

No doubt I'd go with a Remington.  Great gun, especially for the price.  My Sendero is the most accurate out-of-the-box gun I've ever owned at well under 1" groups with factory ammunition.  Don't skimp here or on the optics - you get what you pay for.  A good rifle-scope combination, if taken care of, will last you for decades.

You're also going to find that there are a wide number of opinions here on caliber selections.  I'll try to be as unbiased as I can:

The .270 definitely has its merits: its realtively flat shooting up to 130 grains, ammunition is easy to find, and it doesn't kick nearly as hard as a .30-06.  The .30-06 is a great round too, not anywhere as flat as the .270, but you can take just about any game animal in the U.S. with it (except big bears).   It has a wide bullet weight range of 150 to 180 grain (some load a round nose 200 grain too).  The .30-06 I owned was a tack driver but it also had a pretty good kick to it. 

Frankly, if you're going to think in the .270 or .30-06 range I'd recommend a 7mm Remington Mag.  It shoots flatter than a .270, is a great whitetail round with 140 grain bullets (available from several manufacturers) or even 150 grain if your rifle won't shoot a 140 grain well (different rifles like different bullet weights).  It doesn't kick like the .30-06 either in my opinion.  Ammunition is as easy to find as a .270 too.

A lot of folks will say the 7mm Mag is too big for whitetail...hogwash.  We're talking about the difference in bullet diameter of 0.277" for a .270 versus 0.284" for a 7mm.  That's 0.007".  To compare, most .270 hunters I know of use a 130 grain for whitetails so that's 10 grains difference in bullet weight.  The key to the 7mm is that it'll sling an equivalent bullet about 10% faster than a .270 due to the case construction.  Also, with the 7mm you have a pretty wide available bullet weight range of 140 grain to 165 grain (175 grain for handloads) so the round will handle all the way from pronhorn to elk.

Fact of the matter is that the best cartridge depends on your hunting conditions.  Since you don't know exactly what that will be for the next 20 or so years you want to get a round that'll handle about anything.  To me the .270, .30-06, .308, 7mm-08, .264 Win Mag, and several others will handle your situation well.  But, if you're looking for a combination of flat trajectory, ease of purchasing, less kick (as compared to a .30-06), and versatility the 7mm Mag is the way to go.