WordPress developers are generally incentivized through hourly client work or part time or full time agency or corporate work. If they are wise, then they will try and build a plugin or theme that serves a market need, so that they can find a path to residual revenue. Getting it out to market, growing usage, and then pivoting and adding a PRO version or some type of service where there’s a monthly subscription is where this has all gone. Matt Mullenweg, co-creator of WordPress (along with Mike Little) estimates the WordPress services and plugin/theme marketplace to be worth over US $1B and growing. Like any open source project, the incentive path to monetization is in becoming an expert in some aspect and then exploiting that expertise to generate income. Then splitting time between the free project and adding features or add-ons to the PRO version.
But, to your point in your first paragraph, there could certainly be a mix of support. I am actually planning my own Kickstarter campaign, so that we can build in the audio player integration with Radio Station, then get that out to market as a freemium plugin, whereas it accepts a file from shoutcast or icecast and then prints either the Show name or tracks into the player as they are added.
Once we get to that point, I think it’s a natural progression to make the integration with LibreTime and then I would, on my site and in the plugins read me and plugin page, recommend LibreTime as the primary radio station automation software for Radio Station. I am going to speaking to the developer helping me with Radio Station about all of this and get his input and feedback.