This used to be a subject reserved for the charting experts and the geeks who got into the nuts and bolts of aircraft performance. Speaking as one of those in the latter group, it wasn't easy to plan a takeoff based on losing an engine and just clearing all the obstacles because most pilots were trained to use their aircraft flight manual engine out data for all conditions. It was conservative, after all. Things have changed.
If the subject of departure obstacle analysis is new to you, I recommend you digest the following, in the following order:
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