There's no downside to soaking. I don't know if that would really make the roots pliant enough to slip them out of small holes like that, though I really couldn't say. Some people might just dump that smaller pot into a larger pot and add some bark around it instead of dealing with getting the smaller pot off, and this totally works. For me, I like to get all old media out, especially with cattleyas, as I want to see if there is any rot or bugs in the media. If I were you, I would cut off the pot as I think that would ultimately only cause minor damage and I've come to accept that there is always some root damage when repotting. I'm a pretty aggressive repotter (as I said, I try to remove as much old media as possible) and my cattleyas don't seem to mind!
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