Honestly, I quite like Python most of the time. The times when I don't, argghh type errors.

The worst I have had in a while is when I was dealing with a sparse array data type and getting some processing done in a C function to speed things up.

Infuriatingly enough, the index type used to change after initialising the array. It would check if Int32 could accomodate the size of the array. If it could it would downgrade to Int32 at runtime. My C counterpart had no clue.

That was so not fun to debug because the errors were intermittent (depending on the fill factor of the sparse array)