I have the iDisplay program running on my windows machines which allows my to use my tablet as a 2nd (or 3rd) monitor. It works great on windows but I keep getting a error about loading virtual drivers after installation of the .exe.
I'm still fairly new to Ubuntu. I saw a work around using a VNC client but it does not allow clicking and dragging accross the screens and seems much more complicated.
It likely will not work like that. Especially if it an Apple device. Wine does not support any drivers, USB or otherwise, so unless it works natively in Linux, it might not work. Have you looked for a native Ubuntu program to do this, without using Wine or POL?