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1. There's a bookmarklet included with OF/iPad to enable you to send a Safari/iPad URL to Omnifocus. So you could, for example, email the url from the Windows machine to your personal email account, and then open it from iPad Mail into Safari.
2. I work in exactly this environment. My top tip is to take the time to set up relevant perspectives on the Mac so you can see exactly what you ant to see on the iPad (you can't create perspectives on the iPad).