I create an autoplaylist and don't change any settings.
This is right after the autoplaylist has been created:

You can see:
· artist column is selected automatically (I didn't select any sorting option, or click on the column)
· numbering starts at #44 and #1 is near the bottom of the screenshot
· the numbering appears to be mostly paired Eg. 44+45, 42+43, 48+49, etc
· the tracks are sorted by artist first, then by album - there are no anomalies - the whole list is correctly sorted by that criteria
The next image shows what happens when I click the # column:

You can see:
· the # are all in order now
· the tracks are sorted nicely by artist at the beginning of the list. However at the end (#2500-2700) the artists are mixed up.
· within each artist, some of the tracks are out of order as shown by the red dots. This happened when the list was
dynamically created. There doesn't appear to be any pattern to it.
Now, when I click another playlist, and then back onto this one, the beginning of the list fixes itself - no more 'red dot' tracks.
However, the last 6th of the list is still all mixed up, as before, and it looks generally like it has something to do with the added or modified date.
So that's what I mean by not getting freaked out by strange anomalies when sorting - it doesn't always do what you think it's going to do, or should do.