Getting started - using written family tree


I have a family book that dates back to the late 1700's and has all my ancestors documented - perhaps 100-200 people. If I am about to begin entering this tree into FH software, can I start with the oldest ancestor and work my way down, or do I need to start with myself and work my way backward?  The book is laid out from the oldest ancestor down.

Once I have all my data in the tree, what are my best options to find missing elements and connect with other family trees?

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