Should I re-re-pot my Dendrobium?

[Lady Oscar]

I recently bought a Den. Samarai that came potted in a 2.5" plastic pot. The newest cane was growing entirely outside the pot and it was necessary to wedge the pot into something to keep it standing, so I decided to re-pot. It has a new cane sprouting, and some new root growth, so now seemed like a good time.

I moved the plant into a 3" slotted clear pot with Better-Gro orchid mix (a fairly coarse mix of charcoal, park, and perlite). Unfortunately, I don't think I did a very good job of it.

I was eventually able to cut the original pot off without (I think) doing too much root damage. The whole thing was basically solid roots, wrapped around some pieces of bark. I soaked the roots for several hours, but still wasn't able to remove some of the pieces of bark because they were just too far inside the mass.

The 3" pot was able to hold the roots and existing canes, but I could hardly fit any new media around the roots, and ended up with the top of the root mass above the top of the media. Also, I'm not sure there's going to be enough room for the new cane to really be in the pot (see picture). Does this look OK, or would it be better to repot into a larger pot?

Thanks, and sorry for the potting noob questions!