B is the way to go. Freeing up disk space is crucial. You don't want your upgrade to fail because you ran out of room. Henry's probably got too many cat videos taking up space anyway.
Hey, did you know that Yosemite is named after a national park? Maybe Henry should take a hike while his Mac's backing up, you know, get in the OS X spirit!
I'd go with option D. Backing up your Mac is always the smart move before a major upgrade. You don't want to lose all your data if something goes wrong.
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