So build your rogue for the map you are attempting. Big maps are amazing for tolling, and waylaying because you aren't becoming fast enemies with everyone on the map, and you can get rich quick tolling.
Smaller maps need more diplomacy, because you cant rely on your tolls, and waylaying as much. So you have to build your character somewhat strategically for the map you are gonna play. Both strategies will work, but if you want to try a one town map, with only 2 other dynasties your gonna have a bad time with being a hated scoundrel. Or for those that love to live on the edge you can amass an army and take any town by force.
In my trials with the rogue I have found there is two surefire ways to win, you can either do things diplomatically and stay away from tolling, and waylaying.
