I’d occasionally have the frustration of not finding what I was looking for, but usually if I combined a search with at least one other operator (who it was from, what label it might have received, etc.) I almost always found what I was looking for pretty quickly.
And as for the signature image attachments thing, I think that’s actually an artifact of how the sender compiles the email, not Gmail. The “has:attachment” operator is one I use a lot and is usually quite reliable.
Hope that provides a little insight!