Interesting list. My "list" (more like wish list) is quite different, but considering what you have and want, I'd go like this...
. Start with DFA 100 Macro. You don't have a real macro, so you must be curious to see how that is going to change the way you do macro pictures. Plus you don't have a prime in that range and it would be very useful for portraits, as you said. This would get a lot of use right now.
. Then go for the Sigma 10-20. You need a real wide lens, but by what you said, you won't need it for another couple months.
. Then DA*55. 50 1.8 is good but this should be quite an improvement.
. Then DA*16-50. Lots of people love this lens and it should also be an improvement over the Sigma in IQ.
. Then the Sigma 70-200. Seems quite redundant with the 50-135 (I'd get the DA*200 or DA*300, but hey, if you need the Sigma, get the Sigma...)
. Finally, the Sigma 85 1.4. For portraits it seems a bit redundant with the DFA 100, though it's quite a bit faster so the bokeh would be nice.
If you're planning this for the next couple years though, my guess is that by the time you go through the first 2-3 items in your list, the rest of the list will change considerably and you probably won't get to some of the lenses you think you want now, because you'll see something you'll want more