Cool you have tersewriter! I have to really get my act together on blogging and I think this might help.
Have you thought about the potential of your suite of products? Thoughtwriter, Tersewriter, the app you use to save things? I would probably polish them up and not charge anything for initial usage. If people want multiple whiteboards, or want to save their Tersewriter blog posts, you could charge for that.
With tersewriter, I'm excited by the idea of creating a platform between Twitter and Medium. It'd have a 300 word minimum and a 450-word maximum. That way, every post is substantial, but focused on just one idea. My main motivation is to create a tool that gets me thinking and writing every day. I figure the word limit makes posting less overwhelming, as with Twitter.
Yeah. I've been thinking a lot about how to monetize the different apps. Together? Separate? What to offer for free, and what to offer as a paid premium. One idea (crazy?) is to charge per day of use, almost like AWS. You'd get 10 days of free use (of use, not just calendar days), and then pay 10-50 cents per day of use. That'd make it nearly impossible to spend a dime on the suite unless it really created a lot of value for you.
I love the Twitter <> Medium idea so much! Only thing I'd want to point out is that some of the best content on Medium is deep, long form articles that really get into the meat of a subject. So you might want to think about that 450-word max.
Re your monetization idea, it seems very interesting but my hunch would be that you should study usage patterns to determine pricing. For eg, off the top of my head, I think that I might use the app(s) actively only a few days a month when I am writing a blog post but it might be super valuable. With the 10 days free policy, I might churn out at least 3 posts before needing to pay.
It's also important to set pricing in a way that it roots the user, even more, deeper into your app. An idea for that could be an affordable yearly license.
For the blogging app, the goal is really to encourage daily thinking and writing, not necessarily to create the best source of deep content.
I do think many long articles should actually be short articles, though. You can say a lot in 450 words.
Per-day pricing seems less attractive to me now. I'm starting to think apps should be pay-for-value, not per-per-use. So, I agree that a yearly or monthly licence/subscription might be better.
Have you thought about the potential of your suite of products? Thoughtwriter, Tersewriter, the app you use to save things? I would probably polish them up and not charge anything for initial usage. If people want multiple whiteboards, or want to save their Tersewriter blog posts, you could charge for that.