I did some searching and didn't find a question that "directly" answered this question.
Anyway the basic gist of this question is I am wondering what "language feature" or "syntax" that makes a language be a major pain to build a parser, syntax highlighting, etc?
This might be subjective but I was thinking of like for example the difference in parsing a language like say Lisp for example with its (func parms etc..) structure, as versus to something like C++ with all of the templates, brackets and so forth.