It doesn’t matter where you start. Just start.
I think you need a dose of OCD to do something as artificial as that. I'd be forever tempted to deviate to have a look at that plant, see from the top of that rock, avoid that bog, and so on.
GeoWizard https://www.youtube.com/channel/UCW5OrUZ4SeUYkUg1XqcjFYA of that there youtube have done that already and a bit more extreme and stupid
Presumably this is not for chickens because it's as the crow flies.
Kim, you are very bad!