How does one appeal to proprietary software enthusiasts? The recipe is very simple. Build a software of any variety, anything entertainment focused is an ideal place to begin. Remove from the final feature set some or many of the basic functionalities that this software would naturally possess. Inform the user that in order to access these “extras”, they must first submit to some demand. This can be anything from subscription payments to in-program status items for their peers to fawn over. Divide it up into many smaller parts, closed software supporters love playing collect-’em-all.
And make sure that it must check in with your master server periodically for good measure. Many proprietary software advocates do not consider a program to be legitimate unless a sort of connected account must be created and signed in before being granted access to the program or its extra features. Tell them that this is a social feature which enhances the experience.
Lastly, always make sure that all of the time and effort which your users will be sinking into this program will be saved into incompatible proprietary formats, ideally server-side, so that they can never leave lest they eat the sunk cost. Keep them ignorant to all of these practices and if they ask questions, always reassure the users that it has been setup this way in order to protect them or to provide better service.
Bonus achievements: