I'm also about to upgrade my wedding kit as I am shooting more for myself lately, not just freelancing/as 2nd shooter for other people.
Currently I have 550D & 60D, Tamron 17-50mm 2.8, Nikon 80-200mm 2.8, & Canon 50mm 1.4.
Here's the kit I am thinking about upgrading to. Looking at used prices on eBay and at B &H I think it should cost me about $2500 all up, after selling the old stuff, to make these upgrades. Going to the mkIII would make the total closer to $4500-5000 which is way over my budget right now.
Canon 70-200m 2.8
Canon 17-55mm 2.8 IS
Canon 50mm 1.4
Canon 28mm 1.8
Canon 85mm 1.8
What does everyone think of this kit? Any glaring holes in there? The big benefits I'm looking forward to are using the 28mm 1.8 on the 5dmkII in place of the 17-50mm 2.8 @17mm on the 60D for dancing, group shots, etc at the reception, putting the 85mm 1.8 on the 60D for speeches as a static shot (rather than the Nikon 80-200mm) so that I can use the 70-200mm to shoot CU's of the bridal table and crowd reactions, and the IS on the 17-55 2.8 (Which is the main reason I'd pick it over a 24-70mm).
It'll also be nice to have lenses that all focus is the same direction!