Need advice for repotting my 'octopus'

[ccrow]

When you look at the photos you can see why I call this phal the octopus It badly needs repotting; it's in its original terra cotta pot, and I imagine the roots that are in there are probably not great, but it has all those other ones which I make sure to soak when I water it. I will be soaking the whole thing in a bucket before I even try to get it out of there; I'd rather not break the pot(although I probably won't use it again- waste not, want not, I guess!). For all you more experienced people out there: do you think soaking will make the roots pliable enough to coax them into a pot? They're awfully straight... maybe I need to try my hand at making bil's shallow pots
What would you do with this not-so-little guy??(I've included a pic of the flower just so you can see)

Edit: does anyone know why my pictures are always sideways?? Grr....

[estación seca]

Look up posts by Helene on her phals growing in big glass vases. I'm trying this with one and I'm already surprised by the good results.