I'm wondering if something that said "Best Value" would be most honest. Or similar remove the "Most Popular" wording and just make that option bigger.

I suspect the answer to your 'wondering' is that the startups have copied what 37 Signals is doing.

If one plan is "Best Value", it implies the others are not.

"Most Popular" is right. It simplifies the decision-making process on behalf of the user. It leads and reassures and solves the "what do other people choose" problem.

I personally think that "Best Value" is better verbiage anyways. When the news about the economy is consistently bad, you can catch people's attention with the promise of value or savings.

You are your first customer. So, the "Most Popular" plan should be the one you would choose for yourself.

Good point. We also considered "Best Value", but that's only the case for the biggest plan.

We finally decided to stick with "Most Popular" and not worry too much about it. But yeah, we might change that : )