I have been doing side-contract work with someone for several years now. Our relationship is great. They are receptive, helpful, and absolutely committed to their project.
However, I'm starting to realize that the project will fail. They have only received several hundred signups in the past 2+ years the project has been up. The execution and goal of the website has been interesting to say the least. Without going into details, they are wanting to add more features to the site. As nice as these features are, I don't think it will save the website. They have almost no revenue stream coming in from the project. I suspect these features will cost them up to five-figures to complete.
Here's my question, I've always let them run their business the way they see fit, helping as much as I can to deliver the best product that they can afford. I have stayed away from suggestions on bigger questions like, "What is the primary feature of the website? What direction do we want to go in in the next six months?" With the gut instinct that this project will never get off the ground, should I tell them what I think?