Yeah, the interface is usually the biggest complaint and I agree it's quite suboptimal. I guess the good bit is once you get something working you don't have to interact with it again until you want to change it.
I haven't tried it myself, but I believe there is a way to write the contexts and tasks in XML files or something similar... you could look that up.
I have often benefited from recommendations for Things I Didn't Know I Wanted.
Given that Less Wrong is a community of unusually intelligent, critical, and self-improvement-focused people, I suspect we can generate a pretty helpful thread of product recommendations — perhaps even a monthly thread of product recommendations.
Rules: