You're right, I agree with you re raising it and the arches. (I'd just been look from the porch to the door.)
On chaos, I happen to like controlled chaos..
on Crape myrtles, a lot of them previously planted in LA had fungus trouble. But new hybrids/varieties have come to the fore with less of that problem. As usual, I'd talk with one or two of the best respected nurseries, and possibly the arboretum people in Portland. I used to talk with the LA arboretum, but, as a designer, and maybe they had an especially helpful staff.
And yes, hardscape, circulation first.
Adds, that looks to me like two risers from the outer landing to the porch, so I'd call it two steps, which is good - one step is harder for the distracted eye to see when walking from the high level.