In case somebody else has this same problem this is what I did to solve. The tricky part was what I had to do in iTunes to find all the busted links to the songs
I downloaded a copy of a tool called "Too Long Paths Detector v4.6". Set the upper character limit in this tool to 245 characters and had it scan the iTunes Music directory. This tool made a text file report of too long paths with full path including song file. Put this report content into Excel, delimited text to columns using "\" as the delimiter, then made a pivot table out of the data, album name for row headers, artist name for column headers, and with count of songs as the data. Had about 10 artists and about 20 albums affected by this problem.
I did as you suggested, renaming albums using File Explorer where I could. A few items had to be renamed at the individual song level. Doing this broke the songs in iTunes, and iTunes had the songs marked with a "!". The crappy part is that you can't sort on the column with "!" so finding each broken song is a pain. I have over 25,000 songs in my library so scrolling and looking is not an option.
Next had to fix iTunes. I created a playlist called "Found", then clicked "Songs", highlighted everything in Songs with Ctrl + A, then dragged everything into "Found". This new Found playlist had all songs in my inventory LESS any song with a broken link. Then created a smart playlist called "Broken" with the following parameters:
(Checked) Match music for the following rules
"Playlist" "is not" "Found"
(Unchecked) Limit to x
(Unchecked) Match only checked
(Checked) Live updating
I then played the first song in each album in playlist Broken. Doing this caused iTunes to pop up a find file box, so I manually found the album or song. For albums with multiple broken songs, after finding the first song, iTunes asked me I wanted to use this first song to try an fix other broken songs. This fixed the entire album of broken songs. I repeated this for each / artist / album / song in playlist Broken.
If anybody else runs across this problem, hope this outline helps you fix up your music inventory!
