A Correspondent writes that he sorts his Music library playlist by Date Added and meticulously adds each new album's worth of files to iTunes in reverse order—one file at a time—so that an album will appear in order (well, the order established for them in the Finder); older tracks appear sorted lower in the Music library playlist than newer tracks. Get me?
Predictably, Our Correspondent is dismayed by the drudgery of this method and inquires if AppleScript can provide any relief. AppleScript provide relief from drudgery? Ahoy!
tell application "Finder"
set selectedFiles to selection
repeat with i from (length of selectedFiles) to 1 by -1
my addFile(item i of selectedFiles)
tell application "iTunes"
add aFile as alias
Save this as a Script Bundle—named whatever you like—to your ~/Library/Scripts/ folder. This will make the script available in the system-wide Scripts menu at the right side of the menu bar. Select the files in the Finder you want to add, which have been sorted in the order you want, and launch the script. It will add the files to iTunes in reverse order so that when they are sorted by Date Added in iTunes they appear in the order you had for them in the Finder.
UPDATE November 11, 2013: Added 1 second delay in repeat loop to prevent tracks from having the same date added (to the second) and sorting arbitrarily.