Key reasons I have the 300/4 IS and EF 1.4X II to use with it are....
1. Shooting handheld... I want IS.
2. Two focal lengths to work with: 300/4 w/o the TC an 420/5.6 with it.
3. Close focusing ability of the lens.
I cannot tell any difference in speed of focus or tracking performance (I'm mostly using on 7D, but sometimes on 5DII, too).
Mostly shooting sports, but also some wildlife.
My 300/4 + 1.4X is plenty sharp, even wide open (rivals the 300/2.8 IS I use when I can set up a tripod).
On 5DII, with 1.4X...
On 7D with 1.4X...
On 7D, without the TC...
I also like the 300/4's close focusing abilities, it's the closest of any Canon over 200mm....
Not that the 400/5.6 is a bad lens in any way... it's a great lens, too! It's just that the 300/4 and 1.4X work a lot better for me.
I wouldn't fret over it too much.... Just get one or the other and go shoot with it. If you like it... if it does what you need... great! If not.... sell it and try the other option. You won't see much depreciation on either lens, unless Canon announces a replacement model at a
very attractive price (unlikely). If bought use, you might not see any depreciation at all (I could sell my 300/4 today for what I paid for it 3 years ago).
On a crop sensor camera.... 300mm or 400mm is a whole lot of lens!
Granted, most birders will say there's no such thing as a "long enough" lens...
500/4 IS plus 1.4X II (on 30D)....