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Might be worth it then - I'll probably do it on 79" (50x17) to make the most of the flat bits.
I did 100km yesterday in the Cotswolds and had to bail once when the speed dropped <7kph, that was 76". Bit of weight loss and it should be fine, at my weight and 10-11kph it's about 2kg per 1.5" gear to maintain the same speed.
Box Hill I imagine would be fine but it's Leith Hill I'm not sure about. I live in Bromsgrove so probably won't be able to make it down to check it out