Upgrade Path

[HDNitehawk]

You will find one without the click, just keep swapping till you do.

Your question was to wide to nail down really pointed suggestions.

This was your breakdown;

• Family events-~25%
• Dedicated "portraits"-~10% (usually friends or family)
• Landscapes-~25%
• Wildlife/BIF/etc-~25%
• Misc-~15%

If I were to analyze my needs I would prioritize them. I would suggest you do to.

I take quit a few portraits, but it is not my passion. I play with lighting a bit and friends and family ask me to do shoots and I take it as a challenge to try.
It may comprise 10% of my shots but the end results are not as important to me. So as portraits go, I have the 100mm macro IS and it does fine for the portraits I would want.

Family events for me are documentation time. When I look back at the pictures they are bringing back memories. I don't know about you, but other than as a photographer I do not remember bokeh. So as lenses go for my kit you would have it well covered for the family.

Landscapes, I like landscapes. It would be my second favorite. From looking at your work over the last few years it appears to be a big focus for you as well. I think you could benefit form the 24mm TSE or the 24mm f/1.4. Perhaps even one of the Zeiss primes. Even though you are buying the 24-70mm II I would still suggest one of the primes. While the zoom may be as sharp the primes still win in other areas such as distortion and flare.

Wildlife, my favorite. Sometimes BIF but really wildlife in general. I know you like it to, and I know that you backpack and as you mention Kayak.
So the 600mm might not be the wildlife lens for you. The 300mm f/2.8L II lens would be somewhat portable, but carrying it on a Kayak? Do you find the 100-400mm to be to large on the water? It would be simple for me, I am land locked and the 600mm or 500mm would be the choice. Size and how large would be to large would be a good place to start the decision process. Possibly even use this type of thinking, if I am in a boat on the water I might choose my wife's t4i and a 300mm f/4 before the others. Why? Because dropping a $2000 rig in the river is much more acceptable than dropping $20K