Keeping things positive.
When it comes to "Stuff" that you can keep on your thumb drives, It really depends on your need.
I have one that is my emergency boot USB and it has Hirens boot CD and a few other recovery tools on it.
I have another which is my "Roaming Workstation" that I have encrypted with "Truecrypt" and it has all my portable applications (from Portableapps.com and pendriveapps.com
Third I have another encrypted drive with nothing but installs, patches and plugins for those time when internet is slow as molasses in winter.
Forth, And empty thumb drive for transferring files back and forth.