The 50 1.4 tends to be sharpest at around 5.6 as is the 24-105. But, the 50 in my experience is not as contrasty, so the images don't have the pop you might be used to.
The 100 2.8 Macro is a great buy, the 100 2.8L IS Macro is that much better for hand held work. For me, I'd say the Hybrid IS would more than make up for the 1 stop speed advantage of the 100 2.
That being said, and your poll asking for a choice of 2 specific lenses with a shift on the second, I'd have to recommend the 50 1.4, so that's my choice in your poll.
Reviewers are finding the new Sigma 35 1.4 DG HSM to be very impressive though, so you might have to revise your scope on things!
Good recap of everything. I would like to express why I own the 100 f/2. For me, it has little to do with IS, and just for the fact that it offers me an entire extra stop of light vs. an f/2.8 lens. This feature comes in really handy for indoor sports. I've recently been to some nasty gyms, and this really helps. I know this is a narrow case, but consider what I did here:
I was forced to shoot at f/2.8, 1/500, ISO 6400 in a gym. Most of my shots were 90-120mm from where I was standing (using the 70-200L f/2.8 II IS zoom lens). I got tired of it, because at super high ISO and proper exposure, the faces of the players lose detail. So I put on the 100 f/2 lens. I lost flexibility, but just went up a few rows in the stands and stood up shooting across at the players. I don't like this lens wide open, but at f/2.2 it seems great. So I then adjusted to f/2.2, 1/500, ISO 4000. And that lower of an ISO made a big difference. The AF was very fast as well.
Just a case where the 100 f/2 came in very handy
Portraits? The 85 f/1.8 does the same thing I described. I'd go for that, as the IQ and low-light performance of the two are very similar. The 85 f/1.8 is pretty darn sharp at f/2.2 and narrower!