I agree with that. That was fixed a little in 2016 when workers would automatically snap to a minimum Popularity if booked by decent to large sized promotions. That was a compromise of a "Big debut" idea that people have been suggesting on and off for years, you know, the idea of someone like an Undertaker or Kane skyrocketing in popularity for a brief moment. My guess is that it was never added because it would be too easy to exploit using save scumming or whatever.
I mean the people who claim to want challenge and stuff are often the same who used the TCW Marat strategy oddly enough.