For the problem of the leading A's, this could be a Gimp bug. The A is obviously truncated in text layer for "Adobe Caslon" (while the text path is OK), and it seems the same applies to "American typewiter" even if it is less obvious because the serif is thin (but its serifs are very wide). Printing a sequence of 'A' and comparing the A's at both ends with the A's in the middle could be a good way to demonstrate the problem.
For Arnold, it appears that the holes strokes are listed before the outlines. Same for Anabelle, but this isn't consistent, this only happens on the "e"'s. I will see if I can improve the algorithm, checking if the bounding box of a hole is completely within the bounding box of the next, and if so swap the strokes.
For Arnold, it appears that the holes strokes are listed before the outlines. Same for Anabelle, but this isn't consistent, this only happens on the "e"'s. I will see if I can improve the algorithm, checking if the bounding box of a hole is completely within the bounding box of the next, and if so swap the strokes.