This doesn’t look so bad, does it? The orchid looks nice and healthy and there are new growth tips on the roots. What could the problem be?
I’m not sure if you can tell, but when I re-potted it, I didn’t have the proper size clay pot available so I used a plastic pot. Bad mistake. Because while the orchid is happy, I am not.
First of all, it continually tips over and that’s really not good for the plant. I have already damaged one of its leaves that way.
Next, when I go to re-pot this plant, I am inevitably going to have to damage some of the roots–and I am going to have to cut the pot off. That’s not good for either of us.
With a clay pot, if I got desperate, I could just have broken the pot away (something that accidentally happened that led to this fiasco).
But check out these roots coming through the bottom here. Not good. I mean, the roots themselves look fine, but how will I ever be able to disentangle them from this pot at re-potting time? Oh boy.
So take my advice–don’t try this in your home!
Gardendaze 
Your plant looks very healthy and repotting shouldn’t be too hard. I have found that it’s easier if you soak it for about a half hour and then it will loosen.
I think you already do this, but I find that my top heavy plants look great when sitting inside a much larger decorative pot or even a larger terracotta. Sometimes it’s necessary to set the plant on an upside down disposable container or terracotta pot inside the larger pot to raise it’s height. The inner pot isn’t visible. My orchids love the added humidity, too, because I can add water at the bottom of the outer pot (assuming it doesn’t have a hole at the bottom) and it adds humidity without the plants’ feet/roots sitting in it.
Thanks for all the great suggestions. I do indeed put many of my orchids in decorative outer pots. One thing always to be cautious of (although this doesn’t sound like an issue for you): you want to make sure that the water level in that outer pot is always below the bottom of the inner pot so that the orchid isn’t standing in water. I know several people who have rotted their orchids completely that way.
I will take your suggestion about soaking when I am ready to repot this. Thanks so very much!
Karla