1º) Install a Windows partition on your mac
I have used Boot camp for it: Boot Camp is a multi boot utility included with Apple OS X that assists users in installing Microsoft Windows operating systems on MAC. Other alternatives to have Windows running on Mac are Virtual Box, Parallels Desktop, etc.
*By default, your mac will run OS X. If you want to choose the Windows partition, press and keep pressed ALT while your MAC is starting.
2º) Run Windows and install your tablet drivers without your tablet plugged. If you have the original CD of your tablet's drivers, use it, if not, go to their official website and download the most updated ones. Follow the driver's intructions to install it and plug your tablet.
3º) If you get Paint tool Sai now and open it, you will notice your pen pressure might still doesn't work, don't panic and install: .net framework: Net framework was created by Microsoft for building, deploying, and running applications and services that use .NET technologies, such as desktop applications and Web services. (My net framework is 4.5. That’s what most people was missing!)
4º) Restart your Mac to be sure everything is working correctly and open the Windows Paint tool sai. Should be working, or at least did for me.
This was tested on iMac mavericks + a Wacom intuos pen & touch + a partition of Windows 7. Good luck!
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