I bought the Mac version of OLLY, which I love. My question is, do I have to buy the iPad version too if i want to install it on an iPad? Or is the license for the Mac allow me to install it on an iPad as well?
They are separate products. Do you have DropBox? You're going to need that in order to sync your data between the desktop and the iOS device.
p.s. I don't work for OLLY, I just had the answer you were looking for.