Why is repotting a new orchid such a pain

[nogreenthumbs]

I bought a Miltassia Oncidium about a week ago. I could tell that it was in tightly packed sphagnum , but I was hoping to wait a bit to repot because it's got an active inflorescence plus a new inflorescence that looks like it'll bloom in a bit. Besides, the nursery that grew him managed to keep him alive, so why can't I? I haven't given it much water and have been waiting for it to dry out and watching a bamboo skewer for wetness.

Tonight, because I hadn't watered in for a few days, I decided to check the roots. I pulled it out of the container and the smell of mold hit me and it was spotted all around the outside of the root-ball with fuzzy green spots of mold like you might see on old bread. Darn it!

So I soaked the root ball in water for a bit. It wasn't as pot bound as my last new repot. I managed to get the sphag out. With this sort of thing, there's just no way around damaging roots, but I figured it was important to get the stuff into a new environment and not take any of the old sphag with me.

What kills me is that once you've gotten the old stuff out and untangled the roots, it's really a pain to stuff the roots into a new, slightly larger pot with media. What's the secret.

This is the old pot and the new pot. It does't look like it, but the black pot fits neatly right inside the new round pot, but getting the roots in AND media is horrible. How do you manage without cramming the roots in and without going up several inches of pot?