It's true that we must always be careful that we're not walking into the Haram or doubtful in our effort to help others understand Islam and that we don't get the wrong message across. However, I think there are certain avenues we can explore to 're-package' things and make them more palatible for the audience we're dealing with, especially when it's an audience that wouldn't be too receptive otherwise. Then, slowly help them work their way up to better understanding and to the state where they actually want to learn things the traditional way.
I think educational kiddy nasheeds have done that somewhat, especially the ones without instruments. Also, more short stories/novels (that teens like to read) based on Muslim characters living in the West could help too, I think, as it could showcase how to deal with situations and set the standard for kids, maybe.
Instead of explaining fiqh rules that can be somewhat 'dry', I think it would be more effective if they were based on real life examples or situations, perhaps in the form of a story.
Those are just a few ideas...