With the current versions of of e-Sword (after version 11 I think) you have the option of saving your resources to a cloud account. Go to the Options menu and select Resource... At the bottom of the pop up window you will see where you can set your resource and user files locations. Click the folder icon and navigate to your cloud folder and select it. Oh, and remember to copy all your resources and user files to your cloud folders first.
I use this feature all the time. I take notes during the sermon on my Microsoft Surface then when I am home I can see them on my desktop. I may prepare a lesson or Bible study at home and then access it on my Surface when I am at church.
I haven't tried this yet, but I think if you convert your study notes and other resources to the topi or noti format you should be able to read them in both your Apple product and your Windows desktop.