As for your additional questions, first I need to tell you that Joliet is not an entirely separate filesystem. It is an extension added to the ISO 9660 filesystem. Thus, when you enable Joliet you aren't substituting it for ISO 9660; you are adding it to ISO 9660. The result is that you can include both long and short filenames. Windows will show you the Joliet long filenames by default, but the ISO 9660 filesystem and its short filenames is still there.
Here is an example of a disc (actually a disc image, but the characteristics are the same) that has some mp3 files. You can see both the Joliet long names... :
... and the ISO 9660 short names:
The naming convention you describe (with numbers last rather than first) will work subject to two conditions:
1. The portion preceding the numbering is the same for all files. If not, then the alphabetical order of the preceding portion will dominate, not the numbering.
2. The total filename length (not including extension) is less than or equal to 8 characters (27 if using ISO level 2)
The reason for the first restriction is obvious. The reason for the second is that when disc mastering software converts long filenames into ISO 9660 compatible short filenames, it generally keeps the first several characters of the long filename, truncates the rest, and then adds something to make the short filenames unique. This is bad for your scheme, because the part you are relying on to order the files is the part that will be truncated and replaced. Here is an example showing Joliet long names adhering to your naming convention... :
... and the shortened ISO 9660 filenames automatically created by the mastering software:
By comparing the file sizes and the logical block addresses (LBA), you can see that the ISO 9660 filenames are in the reverse order of what was desired. Thus, your tracks will play out of order. Stick with keeping the numbers first, even if you don't quite like the look of it.