I doubled my position in ITIC yesterday. I also have another bid to by more.
My broker is lending me the money to buy the stock, also known as margin. I may play a trick on my broker and buy more than they would feel comfortable lending me. I didn't participate when buying everything on credit was in style and I want to experience that.
I think there's something in what you say about mgt. For example why have dividends been so low w/r/t the industry for so long?
What mitigates the problem for me is that the Fine clan have large chunks of stock.* (Don't take this on faith--in case I've made a mistake or something please check the footnote below.)
So, no, they may not help me sell well in a particular year. But they also don't buy in shares at high prices, they don't waste money on speculative nonsense (that I know of!) ... in short they're in the boat. To me that seems good.