Looks like you have a bit of Mesuki to do on these. (reduce summer foliage so the sun can get into the interior areas).
It seems to me like you can immediately get right at is as you are in Portland and I do it now up here in Seattle. This will allow you to plan your future styling. I can't totally tell right now, but it looks like you have the potential for the start of a good trunk already, if there isn't another trunk on the far side of the photo.
In Feb you should be able to repot (if you have a cold frame or garage for good after care) and do your first shot of partially cutting through (and cut pasting) the 2 roots I see that are the very worst.
Having more then one tree gives you lots to experiment on!
You might want to check out this care calendar by Darren Wong, remember that you'll have to shift dates a bit earlier in the fall and later in the late winter/spring as its from the Northern California area. I'm not a big fan of all the chemicals, but Darren gives a good starting point for you.
I've got an azalea order coming in from Van Veen Nurseries today. This includes, amongst others, a couple Rukizan - one younger, one older. It will be interesting to compare the form of these to the ones I received from Nuccios last month.
cheers and have fun!
DSD sends