Some of the challenges I have seen with this:
We front load the roadmap with core features and then our key differentiators are in the back.
The problem I have experienced with this is that we lost their attention once they felt their immediate needs were solved.
We focus on top 10 features and at times the features are unrelated to each other. Makes the value progression move all over the place.
What other challenges do you experience?
The biggest challenges we have had are;