I think the free plugin + paid addon model makes sense. Businesses like Easy Digital Downloads and WooCommerce prove how successful it can be. I believe for this to be successful, the free plugin should be functional/useful to a certain extent. For example with EDD, you can sell things with a PayPal check out for free. If you want things like recurring payments, content restriction, other payment gateways, you can buy those if you need them. As for the sustainability factor, each of them do charge recurring fees for ongoing updates and support. This is a pretty common theme amongst most theme and plugin business models these days. Here are my thoughts on other plugin business models: The ACF Model Advanced Custom Fields used to run the addon model like you described. Give away a very useful plugin for free. Then charge for individual addons. Then, they switched to a "Pro" model1 in which they bundled every single one of their paid addons into one paid plugin, no separation. They continue to give away the free version, which is still wildly popular. In my opinion, their Pro plugin can probably be sold for much more. But perhaps the low price point makes it an "impulse" purchase for many
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