As I improve the application, would it be reasonable to mark some features as "pro", but not charge for them yet? The idea is to let users know that these particular features are free for now, but will eventually require a subscription.
I suppose I could include a checkbox to "enable" pro features rather than label them directly.
If you are going to charge for the features, you should not make them free, even to begin with. By doing so, you create an initial value in the users' minds of what those features are worth... $0. If anything, charge for the Pro features and gain a good user base (though you might not sell a single Pro account), and then have a one-day special where users can sign up for a month of Pro for free (or something along those lines). This allows them to get a taste of the Pro without eroding the perceived value.
You might also consider making the whole thing free and asking for donations to help you keep the project going and continue improving it and adding features.
As far as building a sustainable business goes, Twitter can't even do that from their own service. It will be difficult at best for you.
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As I improve the application, would it be reasonable to mark some features as "pro", but not charge for them yet? The idea is to let users know that these particular features are free for now, but will eventually require a subscription.
I suppose I could include a checkbox to "enable" pro features rather than label them directly.
If you are going to charge for the features, you should not make them free, even to begin with. By doing so, you create an initial value in the users' minds of what those features are worth... $0. If anything, charge for the Pro features and gain a good user base (though you might not sell a single Pro account), and then have a one-day special where users can sign up for a month of Pro for free (or something along those lines). This allows them to get a taste of the Pro without eroding the perceived value.
You might also consider making the whole thing free and asking for donations to help you keep the project going and continue improving it and adding features.
As far as building a sustainable business goes, Twitter can't even do that from their own service. It will be difficult at best for you.