Oooh, good choices with the 16-35 and 100L
I'll stick my last post, 135L and 85 f/1.8 for portrait recommendations. You should get both for around/under $2k. Only doubt for me is if you consider them to be a bit close in FL to the 100L, but that's for you to decide. The 100L can do things they can't (macro), but they're faster.
Food for thought