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Why not start at Crianlarich (there's a train station) and continue on past Fort William up the Great Glen Way to Inverness?
a lot of people don't rate it but i like most of the WHW and have done it as a whole and as single sections over the years, all weather with no map reading needed and well spaced rest stops.
i would say S->N. although you lose a lot of "gnar" by climbing/pushing devils staircase and the path out of kinlochleven you gain mostly longer faster smoother desents. and you end up in the highlands not in milngavie.
unless you really want to say you have done the full thing i would start in crainlarich as the previous 50miles are not worth it for the hard work along a lot of lomond and the boring farmtracks leading to it.
unless you are super fit the 50miles from crainlarich to FW would be tough for most in a day never mind the full 100.
if you have 3 days free (40-50miles a day)i would suggest the cairngorm circuit instead, not as tough and still very good.