> Are those dark markets contracts enforceable?
Of course they are. When absurd laws try to prohibit market forces, shadow markets emerge and they tend to have their own enforcement policies. Think mafia, prohibition in the 20s, corruption and stuff. Things get ugly, but they get done. The point of having regulated markets is precisely to put some order and fairness into this.
> This is a perfectly market oriented solution, if you don't like the idea, don't buy this kind of shares
It is not, and the problem is that if that idea were to become popular, then capital would become more and more difficult to buy. So yeah, it's a step towards communism indeed. In the end, it's all about adding restrictions to the circulation of capital.
You can't artificially attach a right to something that would depend on the duration of ownership. In a free country, you can buy and sell stuff, which by definition means their value can not depend on the duration of ownership.
Let me make that reasoning clearer. Imagine I've owned an object for an extended duration, and that this extended duration gives it an additional value V. In a free market, I'm supposed to be able to sell this value V, but if I do, then the buyer will own this object with this extra value V, despite the fact that he's just bought the object. So your initial goal of giving value to duration ownership has been defeated.