Needle Drop File Naming Practices

I've had a Sugar Cube SC-2 Mini for about a month now and I have been producing a ton of needle drops. I had made a few in years past, but they were used only locally on my Mac. This time around I plan to use them in my car (2019 Jetta) via Car Play. I have a Synology NAS that I plan to use to access these files both locally and remotely when I am away from home. I have some file naming questions for the experts here.

1) I like using chapterized AAC files where the entire side is one file and you can access the tracks via a popup menu in Quicktime. It keeps file management simple with one file vs. many. Now I realize not all playback software gives you the ability to access the individual tracks this way, but they do play the entire file back. Have any of you run into issues with chapterized AAC files?

2) The files the SC saves out are named using the artist name and track name. This makes for some super-long file names that get truncated for display purpose in the Mac Finder and in some playback software. There are ways to get them to display, but it is extra work. Where I am using a single file for an album side it really isn't necessary to have the artist name on the file. I cold see where this makes more sense when making individual files for each track. But what do you do in this case?

3) I notice the SC-2 changes file names with "quotes" to 'apostrophes'. It doesn't seem to change punctuation marks or anything else. Back in the day all of the various operating systems had characters that were illegal. It is much better these days. Track names have every character undertake sun. I was wondering if anyone knows of any characters that are still trouble.

4) I use Fission for track splitting purposes when making my AAC files it has field for Track "X" of "Y" and Disc # "A" of "B". It starts getting tricky when you have more than 2 disks. I have been treating each disk separately, so if I have 3 discs with 12 tracks each I number tracks on the first disk 1 of 12 etc. I start over again for the second disk. This as opposed to ending up with numbering like Track 23 of 32. How do folks handle this for multi disk sets?

Thanks in advance for the help. If there are any other related "No-no's" you can think of, feel free to mention them.

 

If I have the full album, and know I want to play it, in order, on a variety of devices, then I'll name individual gapless tracks similar to the metadata download from CD ripping:

The Aquabats - Charge!! - 04 - Tiger Rider Vs. The Time Sprinkler

The only thing this won't do is play albums in chronological released order, but then, metadata/library-based players don't respect such an option, either.

I've got piles of 12" singles, though, different remixes of the same track, and usually the contents of the whole thing go in their own folder, with, of course, no album.

 

I manually cut mine, title them 01,02,03... and so on.
Use mp3tag utilizing the discogs submission number to name them.
One I did yesterday-

 

What @c-eling said. Quicktime and "exotic" file formats are to Apple-ish for me . I record to WAV, denoise and declick using Audacity, split the tracks into individual files manually by the scheme ##-TITLE.wav, and then use command line lame for converting to high-bitrate MP3. From there I ID3 tag them with MP3tag which I instruct to assume the above naming scheme. If applicable I add artist, album and cover art for all files in a directory manually. (I also use _ instead of blanks in filenames because I hate filenames containing blanks, and instruct MP3tag to convert all _ to blanks in the tag, but that's just me).