CRM stability checking prior to version(s) update(s)

We presently run our CRM on version 7.7.8 and wish to update to the latest version. Two things here:

A: We understand that a stability check must take place beforehand on our CRM, i.e. prior to any update. Do you have any guidance on how a thorough stability check is done?
B: We also understand that the version updates must be gradual. Do you have any guidance referring to the version that we are at and how we should proceed gradually?

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I think this covers just about everything you might need to know