I was thinking to take a trip to PE but stopping along the way to work at places like Swellendam, Caledon, George, Knysna (I'll give Mosselbay a skip though). Would it be worthwhile? I suppose in George and Knysna, ESA is known but what about the smaller towns? And how does one go about advertising (besides on the forums) that one will be in that town? Not everyone reads the forums. I can do with some advise please.

Well, for the PE trip, start mentioning it on the thread that's been running for a few years "Port Elizabeth - Top 10". Try to engage the punters now and keep them chatting to you on there until you arrive. That way we can cat to know you, budget for your trip and have no excuses when you arrive.
I would suggest you do the same for the other small towns. Also, ask other ladies that have traveled for the best places to work from.

Good luck and consider me a guaranteed PE punt

All the little towns you mention- if you're going to be there for maybe holiday or some R&R, and your focus isn't primarily on business, then it's fine. The exception might possibly be George. There might be some money to be made.
The dorpies' guys don't book in their tuisdorp. Everybody knows everything happening there. When doing the little rural towns you are primarily catering for guys who happen to be passing through for business or leisure.
I have a regular client who does business in the swellendaam Caledon, Struisbai, Bredasdorp area and lives in Waenhuiskrans. I was invited to a wedding in Caledon and I thought I could make a working holidayof it and he told me just to go to the wedding and not even bother to work there. Well I didn't bother attending the weddings either. The guys from there punt when they go to the city for work or something.

Gretchen. When are you planning to be in Knysna?