I think a more fun way to add an entrepreneurial aspect to the game would be to create something like a stock market.
Each town has it's own economy, so why not take advantage:
- for instance you could invest in a weapons store, that store will get better weapons.
- If the economy starts to fail your stock will most likely go down
- Death of the owner has a negative effect on the stock
- killing a traveling merchant MIGHT have a negative effect on your stock
- Buying and selling to the store has a positive effect on your stock
- Major crisis (like an imminent dragon attack) could have negative effects on your stock