Originally Posted by H-ost
Fences are awesome but I find that I never remember where they are so I only sell to the main one in the ragged flaggon and anyone I happen to run into.
I've also read that once you invest in teh trader at Riverwood, his cash stores become MUCH higher. Further that his cash respawns every 24 game hours.
You can also marry his sister who will continue to work for her brother but will give you 100 septims a day.