Food - there's plenty - quite enough to keep you going all the way round - sandwiches, biscuits, rice pudding, doughnuts, fruit, sweets, hot dogs (uurgh), etc, etc. Not all of these at every checkpoint though!
Road route choice - I've tried lots of alternatives over the years - not many give much time advantage. The only stage where I differ significantly from the 'official' route is Walker Barn to Whitely Green.
Grouping - it does happen but it's not happened to me when I've run it (and I've always finished inside 12 hrs). I have the impression that walkers are grouped at Earl Sterndale from dusk onwards so that they are in groups before the tricky sections to Brand Top and Cumberland Cottage. I suspect that if you arrive 'at a run' you'll not be grouped but if you really want to know you could contact the organisers.
HTH, Steve







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