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Henry is right about the distance/hill compromise however in retrospect, having had a ganders around the lakes after the event, I reckon the direct Ambleside route wouldn't be too bad with a bit more training.
In terms of doing it in two days of equal 188 miles, I think it is doable under certain circumstances.
I'd like to have a stab at it with full support i.e a team car full of proper food and fluids. I reckon if I trained towards 12hr races, I'd be in with an outside chance of making it within 48 hours. It would be incredibly tough though.