I currently own the 70-300 IS USM and a Kenko 1.4x teleconverter. I use both crop and FF bodies. I have at one time owned the 70-200 f/4 IS and 55-250 IS as well.
I recently shot a wedding where I was able to borrow a Sigma 70-200 f/2.8. I used it extensively for portraits on the 5D and then during the ceremony on crop for reach. The zoom was really convenient to use for the portraits.
However, most of the time I want a lighter lens that I can bring with me for hikes and traveling. The 70-200 is probably too big and heavy for that. Plus 200mm is not that long.
I also considered the Tokina 80-400 for extra reach when I only take my 5D.
So I am considering one of the following options:
-70-200 f/2.8 only. When I travel, put the TC on my 24-105 or 100 macro. (It works on both). I have a hard time with this one because I envision myself not using it as much due to the weight.
-Keep my 70-300, use 100 macro for portraits when the need arises.
-55-250 to use on my crop only for travel, 70-200 for portraits.
-55-250 + 80-400, use 100 macro for portraits.
Sigma 70-200 f/2.8
