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SUBMIT YOUR IDEAThat was fun!
This was a bit of a head scratcher at first. I though there may be some clever way of using the spatial tools to extend the lines - and then thought that maybe Mr Pythagoras could help - which he didn't (Long and Lat are not the same unit of measurement). Eventually I decided on a solution that simply used a ratio to extend the points 5 miles in the correct direction - which turned out to be a very simple workflow in the end.
Didn't use a macro to complete. Used angle to determine new points which makes the answer just barely off.
Similar to approach to what most others seem to have achieved by doing the 'lollipop' approach.
Took a flight, some noodling and getting stuck in Newark airport to finally get this one across the finish line.