1. Sure can, even though the .338 Win mag is based on the short magnum 2.5" long case as opposed to the "full length" magnum case of the H&H version. Remingtons actions are long enough to fit the 2.850" case. Layne Simpson simply rebarreled a Remington 700 when he devoloped the 7mm STW cartridge, (The same 8mm Rem case necked down as opposed to necked up to .416.) As a side note I just went down in my safe and tried a .358STA in my 700 7mm mag, plenty of room.
2. The only thing I could see doing extra would be to purchace a new magazine follower and a different magazine spring.
3. Is it worth it? Thats up to you. A good rebarrel job is in and around the price of a new rifle. You will have to get the prices on the work and check it against a new rifle. That should pretty much take care of that decision. CRASH87