Wacom Pen Eraser side button doesn't work with WinTab?

Windows is so ‘helpful’ that it makes me want to kick it.
These are Windows Ink and System level related UI interactions that are all part of the ‘service’ in case you just happen to need any help or advice or access to further facilities.

That deadzone is annoying and you can do a double tap touch then slide to avoid it.
I managed to get rid of the annoying white circle and ‘helpful’ menu that appeared if you hold the tip still for too long by following the advice in the last reply here:
Circle appearing when i try to draw and its a lot more laggy than before?

The ‘Remove Windows Circle’ link in that reply may be of use or interest to you.

Along with @EyeOdin , I think you should learn to use the excellent facilities for brush preset changing/swapping that are provided by krita.