Scott, maybe you could create a junction point for the itunes bloat.
http://en.wikipedia.org/wiki/NTFS_ju...ing_disk_space
If you move the itunes directory to the spinning disks and then create a junction in C: where it was, pointing to the new location you should be able to reclaim your space.
If you do decide to go for a larger SSD, there is a wealth of information in this recent article.
http://techreport.com/articles.x/22358/1
And hey it's only 13 pages long.
You have the coolest projects.