It's not possible with Strawberry. But should be pretty easy to script using bash, just an find command with mv and some regex.
If you don't know find and regex, you can try a program called KRename: https://userbase.kde.org/KRename
You can't use Strawberry to copy the files back. But if you got an old model that you can mount in Linux you can copy the music from the IPOD/iPod_Control/Music/ directory then use strawberry to organize the files back into normal directories and filenames.
Fading won't work properly without dmix/resampling on Linux, that's why the option are disabled when ALSA is used and a device is selected. Because when fading, 2 tracks will be played at the same time and that's not possible without resampling. If you select ALSA but automatic for device or use pulseaudio fading will work since then the audio is resampled to 48k.
I have never tested with an iPod Touch. But there are issues related to the library imobiledevice that is used by Strawberry.
You can try to start strawberry from the terminal and see if there are any output.
Also running strawberry as snap has restrictions, you have to connect the correct plugs/slots.
We don't really have that. But you can select all songs in the playlist with CTRL + A, then right click and select queue, it will show a number in blue on the right side of the song title. However this will go away when the song is played.