I don't know if you ever played Civilization IV, you may want to draw inspiration from its random events system. In Civ 4, random events occur after certain conditions have been met (e.g. if you control a forest, there may be a forest fire; if your civics of choice is slavery, you may have to deal with a slave revolt; etc.). Some random events are inevitable but for others you have options as to how to react (e.g. crack down on the slave rebels, spend money to save the forest, etc.)
The civfanatics forums have an article listing the events, what causes them, and what their consequences are.
http://forums.civfanatics.com/showthread.php?t=236727
Adapted to TOR, one could imagine the following random events:
- Feud between two families working on your holding (production is down as the two families spend their time quarreling and stealing from each other; you may have to intervene to settle the dispute--maybe pay a weregild to calm things down)
- Theft/sabotage (kind of the same event, but can be used in a broader sense)
- An ancient artifact was uncovered while building an improvement on the holding (treasure from the Second Age, family jewelry from a Dwarvish family who fled Erebor, etc.)
- The blacksmith's son is a very talented apprentice. Spend some treasure for his training and he may become a master smith.
- Wedding. One "prominent" family living on your holding is arranging a wedding with another prominent family of another holding. This may be a good occasion to extend your influence.
- Merchants want to establish a regular trade with Erebor/Dorwinion/Dale/Esgaroth/Dol Guldur. Hire them and you may recoup your investment in no time.
Other possible improvements for the holding (sorry if I repeat some that have already been listed):
Windmill, watermill, roads, irrigation canals, sheep farm, horse farm, smithy, shipyard.
To be continued.
