With regard to the low dividend payout, my guess is that it has to do with taxes. The Fines have pretty good compensation so dividends increase their taxes. This isn't so bad currently because of the Bush 15% tax rate on dividends. However, if that rate expires, the Fines could be looking at a nearly 40% tax rate on the dividends they receive from ITIC.
In addition, because they control ITIC, they can do what ever they think best for their money within ITIC, so why subject their share of corporate earnings to another level of taxation by paying it out in dividends. This is the situation faced by all people who own enough shares of a corporation. They seek to maximize their wealth with respect to themselves and the corporation they control as a group.
1. Yeah, your last point dredges up something I read a long time ago. Maybe Graham? It says that for the control folks, even if they do own a lot of the stock, paying a dividend is at best moving money from one pocket to another.
They ever want the money sometime, there it is.
2. The valuation I tend to use for ITIC over the long term is book value + loss reserves. For the past 25 years the share price has crossed that book + float number again and again. Fingers crossed, because that's a double from here ....