No need to over-analyse this.

The usual preparations should be taken before an upgrade - clean up any apps you don't want, empty the bins, scrub temp files (OS X tends to copy everything, so having a clear-out can reduce the amount of time upgrading takes), run one last disk check to make sure everything's tickety-boo.

There's always YaBingle! for when something unusual happens.

And yeah, don't buy any more books. Those "missing manuals" are very good but they're really a bit excessive for non-intensive use. I can see them being very good references for educators.