244-166 =78
78* 24 = 1872
So it would take roughly 2 seasons for the salary variance to equal out. Assuming they stay with their relative nations for merchandise reasons.
In general I believe salary efficient players are sometimes overpaid. The most salary inefficient players tend to be very old players that are losing skills. However, because you can buy them so cheap they end up cheaper than the younger player.
The other consideration is when you are cash strapped or building an arena still, the more money you have wrapped up in your players means the less you can spend elsewhere...mainly the arena is the tradeoff. That is why Utopia is full of aged veterans.