I only listen to podcasts so you got the big ones: playback speed and remembering position.

Do you intend to support podcasts and audiobooks? Specifically, remembering it stopped playing? If so I will totally drop Finamp for this

What’s your goal? Is it safe to match is a very open ended question.

Take RHEL, it’s meant to be a paid distro for enterprise, something Debian isn’t. But you could draw similarities too.

What’s are you trying to learn?

I think the key is you need to find FOSS software that works for you before migrating your OS. Most FOSS software will run on windows and sometimes MAC.

1-2 and 3 will be hard. You can find many tools that do something similar but it won’t be perfect. There are a few different music managers, and for office libreoffice is the go to.

4. try digikam, it supports all OSes

5. googling “Fujitsu snap scanner Linux” yielded a few blog articles on the matter. Seems it should be supported.

Agreed. You need to be willing to migrate to FOSS software or else “switching to Linux” will be a total failure.