This just tickles me. I love these solutions that are really just an opportunity to learn.
This gave me the idea to score a pair of anagrams according to how many chunks one had to be cut into in order to rearrange it to make the other one. On this plan, the “cholecystoduodenostomy / duodenocholecystostomy” pair would score 3, just barely above the minimum possible score of 2. Something even a tiny bit more interesting, say “abler / blare” would score higher, in this case 4. Even if this strategy didn't lead me directly to the most interesting anagrams, it would be a big step in the right direction, allowing me to eliminate the least interesting.