I agree that the data model is suspect. I'm trying to convert from Oracle to Postgres and changing table structures is not really an option for me. I tried casting the null, ... same problem. It does not like the undefined record type as David is saying. I will try his solution and let you know how it goes.
Just guessing, and don't have time to verify, but you might try casting the null value in the WHEN clause to the same type as the question_set_dir_map_key column in the ELSE clause.
I'd probably also try doing this with two separate indexes; this feels a bit like it might asking the one index to do too much.
