There are many people who just expect freemium to solve all their problems. Freemium needs to be carefully applied, and needs to make sure to be aligned with evaluation needs of potential paying users. Most times startups do not work on the details to make it happen.
30-day evaluations are really helpful when an urgency exists to use a product - in my experience for lots of business sales. But now-days I often get distracted with some project and am not really able to evaluate the product the first time around.
I look at freemium as an evaluation license for as long as you are not doing anything serious with the product. Ofcourse, you need to define the terms of the freemium part. Companies like Heroku do a great job with it.
(I run gondor.io so I understand :-)
Yes, bootstrapping freemium is hard. I would love to see discussions on how to do it right.
Don't get me wrong. I am revenue driven. I am not crazy about freemium. But I see way too many entrepreneurs not putting themselves into the mind of their target users.
I would trivial Gondor.io as a more specific Python oriented version of Heroku. The benefits are hopefully more obvious, and I would argue that freemium is not important for Gondor.io.
However, the problem I have had with micro-blogging platform is in the details, which often results in me not using it more than twice or thrice. I would easily pay $250/year if ThoughStreams worked for me, but I don't know that. Currently the site looks great and it makes me really want to try it, but I doubt that I will be able to make a decision in 30-days. I am willing to try though.
Best of luck!