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I wish, unfortunately I'm looking forward to an austere summer this year...
@skinny yeah absolutely, plus they're walking distances so it'll be down shitty paths but it still could be useful as an approximate comparison between the different routes.
I quickly had a look at the FB page so you've got to hit every checkpoint whilst it's officially open to be in the GC. However, have people in the past missed a checkpoint deadline but then made latter ones in time been put into the GC? I guess it's a different circumstance if they were doing the checkpoints as intended.
I do see your point about gaming the race, but part of the Transcontinental's appeal is that it's interesting to see the large variation in route choice and brings in the more tactical elements rather than just cycling really fast all day and night. For the spectators, it was pretty interesting when in '15 people headed for the ferry and in '16 when Hippy and Frank ditched the conventional route through the Alps and went from CP2 to 3 via the Po Valley.
It also means that it becomes more competitive as given more route choice there's a higher chance there's flatter course better suited to a 'TT-specialist' whilst the skinny guys can enjoy the scenery in the mountains :)
From the organizers perspective though, having people do the checkpoints in any order would be really tough on them in terms of driving. Also, it would be difficult to keep an eye on everyone if some people are heading across Germany whilst everyone else is heading South East to the CP1.
And maybe even Geraardsbergen - 3 - 2 -1 slither down into the Po valley and down the Adriatic to 4.