Interesting. Do you have refs? I would like to read up on this. If not what time period do you refer to?
I don't quite understand what you are arguing about for the rest of that comment however. We don't want our Skyrim economy to be based on bartering! Currency is important. The debts you were referring to were still denominated in some form of currency. Debt is just an temporal expansion of the supply of money. It just greases the wheels of commerce. I don't think is was Adam Smith and his ilk that decreed coins to be of value. Your previous statement indicated the importance of currency in those early days, but more importantly the shortage of specie and thus the necessity for credit.
Anyways, how will you calculate interest rates on these debts? If your character is new in town I doubt he will have the best credit rating with the local S&L.
The book I'm reading now is http://www.google.com/products/catalog?client=opera&rls=en&q=debt+first+5000+years&oe=utf-8&channel=suggest&um=1&ie=UTF-8&tbm=shop&cid=2832048402831789701&sa=X&ei=iBTQTv_CLInHsQKDzrHkDg&ved=0CE8Q8wIwAg. In it, one of the major points of the book is debunking the myth that before there was coinage everyone relied upon barter. Rather, coinage is unnecessary in an economy, as all money is functionally just credit and based upon faith, whether it is in the form of digits in an electronic bank account, paper money, stocks or bonds, or actual metal coins.
In fact, in the earliest form of economies, there was no need for money at all.
If you are stranded on a desert island, with no civilization to fall back on but what you build yourself, and you must rely upon your fellow stranded survivors, what is the first thing you would do? Would you need to set up some new arbitrary money system so that the survivors could trade what food they could find amongst themselves? Or would you work as a team and share what food you could scavenge with one another in the knowledge that someone who was unlucky and caught no fish today may be the guy who catches plenty of fish tomorrow when you catch nothing?
Societies like some of the Native American tribes in the Great Lakes region would actually just put all resources not being personally used into warehouse longhouses, where the distribution of material goods was allocated by votes from the Women's Council. There was no need for purchase, your "credit" in the "store" was that the more goods your family contributed to the greater wellbeing of the group, the more standing your family would have in the community, and the more say your family would have in the councils that determined the distribution of material goods as well as public policy.
The same thing is basically true of ancient Scottish Clans or small nomadic tribes in the ancient Middle East, the notion of money is unnecessary (and the group can essentially function as a "communist" society in the sense of property being communal, not in the "Communist China" sense) provided you meet one very demanding criteria: Everyone in the group knows and trusts everyone else in the group. This was easy in early societies, which were basically all big extended families of no more than 100 people that you would spend your entire life with. It's when you start doing things like building cities or having long-distance trading that you need to start dealing with actual trade with someone who you don't really have a chance to know. The reason that type of community worked without money is because of the same mutual interdependence that exists in that desert island example I mentioned - that form of "communism" works because nobody screws over their community for their own personal gain because A) they're family, and

they're the only support they will have in the world (as other communities will see them as suspicious foreigners), and as such, screwing the community is screwing yourself.
WITHOUT being a member of the community, you would have no vested self-interest in ensuring the community survived, which is why you start to need things like barter or money - if you couldn't trust the other party, the whole contract had to be fulfilled right then and there on the spot. You had to come to some sort of agreement of equivalent exchange.
This, however, is only how people behaved with other communities, or in the rare large city. In medieval times, in the typical small village of people who were generally part of a few intermarried extended families, most people wouldn't really need money, as they traded only inside of their community, and only had to resort to trade or barter in the presence of outsiders like merchants or taxmen or travelers. The typical farmer, then, could simply go up to his cousin, the blacksmith, say he needed a new horseshoe, have it made, and pay his cousin back by giving him a share of his crops when they came in from the harvest of the fields. No need for a formal contract or payment in gold coin, they know each other and trust each other, and they are mutually interdependent upon each other.
The way in which medieval trade in general worked was also along those lines - tax and trade were often based upon credit, not cash, and credit was based upon trust and honor and standing in the community. That's why family and honor and keeping one's word are of such vital importance - unlike modern times, your perceived honor was actually part of your purchasing power, as well as standing in the community.
For a player, who is not just a stranger, but also potentially some strange outlander of some foreign race, to walk into this, it does make sense that nobody trust them unless they have some good collateral or the player pays in cash. This would mean that the player could go into debt, but this debt would have to be backed by something that really had some meaning to the player (like using one of their houses or their title as Thane or ownership of the College or something) as collateral. The game would have to determine the interest rate to charge the player upon a perceived risk, effectively giving the player a credit rating.
As for how interest is charged the player, I would have to say that it would probably make the most sense to make interest a weekly phenomenon, and non-compounding, (as that would only punish those who become late in payment to the point where they would probably just uninstall the mod,) because, although daily interest would make the most direct sense, it might be difficult to actually differentiate a .9% daily interest from a 1% daily interest rate. Plus, even if you have the option to pay for several days in advance, it would be odd that a single dungeon crawl could involve multiple days. (Although I think a slower timescale might be called for in this mod.)
The use of interest and debt would probably be best applied against either guild-leading players, or else players investing in businesses other than their own personal adventuring. This might be achievable through simply making the numbers the player pushes around simply too huge to completely pay off on their own, without using the assets of the guild or the business.
If you take a class on finance, you'll see that basically no corporation in the world runs without an awful lot of debt, in fact, nearly leveraged 1:1. It just makes financial sense, ultimately, as bondholders are simply cheaper to satisfy than shareholders. It might, in fact, be a major achievement or goal of a player to be a free-and-clear single proprietor of some major trading company. However, such a feat would have to require gold in the tens or hundreds of millions to purchase a major trading company.