Yes, the 400L is an upgrade in IQ and speed. For most people, I think it is an either or thing. Some keep both! Only you can decide if keeping both (I think that is what you mean about a $1000 upgrade) is for you.
I think for a majority of people the zoom would be a better lens, as the zoom is more "versatile" than the 400L prime. You need to decide for yourself, what is best for you. Though looking at your gear list, I'd say you like the zooms.
Stick with what you have, if you can borrow a 1.4X from someone and see if the IQ is still good enough for you. If it is see how well you work with manual focus, as you will lose AF. A monopod might help while MFing. If you like it, buy one. If you don't like the IQ and/or don't like the MF, then use the zoom without the TC.
Unless you are made of money or this is how you made your living (and you'd already have what you needed then), I don't see a real need to buy more than the 100-400L.
As Snydremark pointed out, renting may also be an option.
Care to interpret the results for me?
