Hi Kirth, nice setup you got there.
For portrait- 85 1.8 (cheaper, shallower dof) or 100L (better colors, contrast, macro, and image stabilization, and slightly longer reach.) Also don't be afraid to use the 17-55 for portraits. Check out the Sig 35, 50l, 85 threads. There are people on full frame taking many gorgeous portraits with these lenses. Your 17-55 on crop covers all these ranges. Personally, I'd use 17-55 indoors and 85 1.8 outdoors for portraits. P.S. while the 100L has better colors/contrast by a bit, it's nothing you can't fix in post in 10 seconds. I was mainly suggesting it as a longer option, an the ability to do macro is pretty cool.
I'd skip the 135...too long on crop, and not the easiest to use without IS.
Telephoto I'd skip completely for now, two lenses are enough when you start and 3 will make your head spin. After owning the 17-55 and 85/100L you're not gonna be happy with the 55-250. I'd skip it altogether and grab 70-200 f4is when you're ready (if you even need it?)