It is a very good question and there is no short answer to it. At Zoho, we have over 25 different products - and all, but one of them, have a freemium version. I'll tell you this - freemium works very well for lead acquisition. But that's it. After that... you still have work to do in product, marketing, sales, on-boarding, etc. In a start-up these all might be the same person, but they are still functions you need to consider.
I'd think about this in terms of your target market. You say you target freelancers - so that's pretty much the lower-end of the market. In my experience selling to freelancers and SMBs, it is not only hard to attract them to your site (you know this - but the PM space is crowded!), but getting them to convert -and stay- is also a continued business challenge in this pace.
Lastly, think of it in terms of your CPA. The moment you're spending tons of time talking to customers, taking them through a demo, doing follow-up, etc... you're just raising your CPA. And that's not just an accounting myth, that eats into your cash flow.
BTW, you're technically right on one point, but historically wrong. Basecamp DID have a freemium pricing model some years ago:
They did away with it some time ago, maybe 2 years? You can read this one of two ways:
- They were using the freemium pricing to get to be well known, and they stopped it as soon as they became successful
- They ran into trouble (Highrise didn't pan out, neither a some of their other products), so they had to turn free off to generate more cash.