1. How would you rechamber a short-action rifle to a long-action caliber without it being a complete pain in the ***? There is a tool called a chamber reamer that will ream the barrel to the specified caliber of choice! As for it being a short action, I shoot a Savage that I helped to build in 338 Lapua on a Savage Target Action that feeds quite well as it is a single shot action. The only time you have to pull the bolt is to eject a loaded round. So a fired 30-06 casing would eject with absolutely no problems from a short action Savage, Howa, Weatherby, Winchester, and maybe a Remington after firing. However I did notice that Remington's have a much shorter short action than that of a Savage, Weatherby, Winchester or Howa short action.
2. Why the .300 WM for 300 yard deer shooting, when I can kill deer at 200 yards with a .17 Rem Fireball? That's overkill. How many people use a .17 FB to kill deer... you as far as I know. How many people use 300WM to kill deer and paper from 1yd to 1000yds... probably in the millions if I had to take an estimated guess. The 300WM is probably one of the most popular hunting calibers from the Atlantic to the Pacific since its inception in 1963. So... in the case of a paper puncher and a deer rifle to 300yds, makes perfect sense! As for the .17 FB... to each his own I say!
3. 6mmBR over a .308 Win? Barrel life won't be anywhere near comparable, and the 6mm is a .243 caliber bullet...Which is not what I would pick for hunting over the .308... I would tell him to pick a .257 Roberts or 7mm-08, or .260 Rem over the 6mmBR for hunting. The 6.5-284 would also make a great option, as Berger makes the 140 VLD's, and Lapua makes brass for it. Though I won't disagree with the calibers you have chosen, the 6BR makes perfect sense. It has better barrel life than the .308. Now I know its hard for you to wrap your head around something better than the .308. (I have 2!) But do some research and you'll see that the 6BR and its variants dominate benchrest. The standard BR has a smaller powder column, and longer neck giving it inherent accuracy and long barrel life. You'll also find that the .243 caliber bullet is very capable of taking deer and antelope size game well in excess of 600yds. Even with the .308 or any rifle caliber (i.e. .17FB), shot placement is essential.
None of your post makes any sense... As you can see, it all makes perfect sense. You have a lot to learn yet!
Also, the .308 Win will make him a better shooter. (Not necessarily)The .308 Win is the best training caliber there is for 1K,(Many trained marksman will argue this and say there are better calibers. The military only use them because they don't deal with change very well. It was developed at a time when 30 caliber was King) because it teaches him drop, windage, and flight times (Try a 22LR, does the same thing... you could also do that with your .17FB). It also has low recoil (Compared to what! a 22LR, 17FB, Bazooka!), uses less powder (So does the 6BR and accomplishes the same thing), is an easy caliber to load for,(So is the 30-06, 270, 7RM, loaded all of them in three powder weights at a set bullet length) and has great barrel life.(No argument from me)