This is what we came up with. As an aside, I find it funny there isn't a Syntax Highlighting option for Applescript on Apple's forums. Lol. Unless of course I'm missing something.
set oldPlansFolderPath to (choose folderwith prompt "Select folder with old plans")
set newPlansFolderPath to (choose folderwith prompt "Select folder with updated plans")
set AppleScript'stext item delimiters to " "
tell application "Finder"
set oldPlans to every folder in oldPlansFolderPath
set newPlans to every folder in newPlansFolderPath
set numberOfOldFolders to countitems of oldPlans
set numberOfNewFolders to countitems of newPlans
repeat with n from 1 to numberOfOldFolders by 1
repeat with i from 1 to numberOfNewFolders by 1
local newFolderName
set newFolderName to name of itemi of newPlans
local oldFolderName
set oldFolderName to name of itemn of oldPlans
if first word of oldFolderName = first word of newFolderName then
set fileName to (name of some file of itemn of oldPlans whose name extension is "tiff")
set oldFile to (some file of itemn of oldPlans whose name extension is "tiff")
set newFile to (some file of itemi of newPlans whose name extension is "tiff")
set newFileName to name of newFile
set the name of oldFile to "Original - " & fileName
duplicate (some file of itemi of newPlans whose name extension is "tiff") toitemn of oldPlans
set (the name of some file of itemn of oldPlans whose name is newFileName) to fileName
end if
end repeat
end repeat
end tell
Josh