My Mudcat includes both experiences of the word!
:-)
Really, I don't see any absolute either/or about it, but I do see that different people have had different experiences of the implied meanings of the word "crutch."

While I see a crutch real or metaphorical to be a tool and use it that way (the word I mean, not the thing, for in real life I use a walker or cane, not crutch(es)), I certainly have heard it used with a pejorative implication, such as Capri's example about cue cards. Using cue cards as a crutch I've definitely heard spoken with the implication that said user is lazy or a less than adequate speechifier for having need of them. While I've heard it said that way, it doesn't mean everyone intends that every time an expression of cue cards as crutch arises, and it doesn't mean that everyone hears the implication even when it is intended. (I, for one, will sometimes miss all manner of subtlety in a conversation, I'm embarrassed to say, naively unaware of the speaker's layered meanings.)