I think there are 2 issues here:
- Developers of open source software (applications?) making money.
- Migrating between applications being a pain!
From what I can tell a lot of people don't really want to use LibreOffice, they're mostly happy with MS-Office, they just want a free version (possibly runs on Linux too).
While this is an interesting topic - its not universal that software projects are always judged based on their compatibility with the defacto-standard.
Most people wouldn't for eg - reject a new video editor because it couldn't load their projects perfectly from their current video-editor. Similar situation for 2D/3D animation tools (of course some basic compatibility is important, its just generally accepted you can't move complex projects between applications for certain classes of software).
Just commenting on this since I think its a mistake to make out all software categories are as entrenched as MS-Office.
To reply to the OP, Not sure there are many good ways to make money besides services and support.
It's interesting to see Krita crowd funding for continued development. Personally I think this works well early on (adding flashy features), but not so well for maintenance (when flashy features need to be updated or re-written )
If this topic were re-visited in the podcast, it'd be interesting to have people from different projects to comment.