What are you doing when you "dig into a problem"? :) I have a feeling the intent was supposed to be pessimistic/negative (as you stated). I decided to have some fun with the words. It leaves a few possibilities as to the meaning and speaks well of what the developers are typically doing in their "problem solving": digging deeper (for knowledge) rather than trying to get out of a hole.

"People who cannot dig themselves out of a hole have never tried digging sideways." - JS Developer