I seem to have this same problem my work and home Macbook Pro Systems. Both are running Mavericks.
The Mouse is a Microsoft Explorer Touch Mouse and I have the latest version (8.2) of IntelliPoint for Mac.
I have a few custom settings configured; the top and bottom of the scroll button are set to browse back and forward, and the middle-click is set to "Handled by Mac OS" which causes it to open links in new tabs, etc.
The problem is whenever I restart the system or even sleep and wake up, when I return those settings are no longer working until I open system preferences and open the settings for the microsoft mouse. The settings do maintain what I set them to -- I never have to reset them -- but they just don't seem to be "turned on" until I manually open the system preferences page for them.
The mouse works, but the custom buttons do not do the correct thing until I open system preferences->microsoft mouse. When I open the preferences I do not need to change anything-- I simply open the preferences window and the buttons start doing what I want them to. And The preferences window always shows the correct settings. The continue to work after I close them until the next restart. It's like there's an invisible "on/off" switch that gets activated when I open the settings window
Any ideas on how I can get these settings to be enabled automatically without needing to do this every time?