Don't know what to tell you on the gapless playback issue.  My newer car
supports Android Auto, so now I can use an android app that supports
gapless, and that solved my issue, which never could be sorted through
the built in stereo in any car I've used.

But, I mostly wanted to write regarding the original sorting issue and
id3.  

I learned that many of the id3 format (v1, v2.3, v2.4) can conflict with
each other.  When I had a lot of mp3 files, I had all sorts of issues
related to my files usually having both id3v1 and id3v2.3.  In many
cases the tags in each space were not in sync with each other causing
all sorts of conflicts.  Additionally, it wasn't unusual for a tag
editor to only show one space.  For instance, MP3Tag will tell you what
tag formats you have, but it will only show the tags in one of the
formats.  This caused issues at one point where I would edit the id3v2.3
tags, but the id3v1 tags would not be edited.  I never recognized errors
because they were hidden in the id3v1 tags that I couldn't see.  I think
I only discovered it when I went to a command-line viewer that let me
extract the metadata in all spaces.

Further, when files had id3v2.4 tags, I would get huge issues because a
lot of software doesn't know how to use id3v2.4.  Needless to say, it
was a mess.  

My solution at the time was remove all id3v1 tags from files and try my
best to make it so all my mp3 files have id3v2.3 tags (removing v2.4 if
I had them too). This eliminated many metadata errors I was having
related to sorting and inconsistent tags.  I'm not sure this is a
solution for the OP (I think moving to ogg or other format is probably
better), but I thought I would mention it because it is easy to miss and
you might pull all your hair out trying to track down a hidden problem.


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