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Figure out if pages are being retired or moved or if urls stay the same. Imagine every url being someone’s bookmark. If they click their bookmark, what happens. Mapping old locations to new locations is one of the biggest priorities. While you van safely let some pages die without a redirect (404s are a natural part of website life) any page that was getting any sort of traffic, should have a response that directs users/bots to a new location. This is not a hardline rule, but general guideline to follow. If you have a product line that does die and nothing is replacing it, figure out which pages have backlinks or traffic in the past 6 months, redirect (301) them to the most appropriate new url and let the rest die.
