I've always wondered what profession could Gregory/Harold take up after he settles down in River City? He's not trained for anything (especially music instruction) and I can't see him working in Dunlops's stables alongside Marcellus. Of course, he could continue to be a traveling salesman, but that would interfere with establishing a stable home with Marian. I'm betting he puts his gift for gab to work on the local newspaper via a regular column. It's as good a guess as any, I suppose.