Everything we try to do to make this general idea work involves a lot of clarifications on the margins that complicate this. So I'm softening on the idea of just taking the guardrails off.
What I'm referring to is that I already traded Lillard for a pick (as I believe you were also involved in a similar transaction), which probably would supplant that rule. Maybe we could just grandfather them?
Again, what I propose is that players selected with a poster's first five picks (hereafter referred to as "first-half pick") be subject to its own special trade rules, but not a person's 6-10 picks ("second-half pick"). What this would mean is if I wanted to trade a first-half pick drafted in the 2010's, I could only trade it for another first-half pick drafted in the 2010's of someone else's. This restriction would not apply to second-half picks which are open season as long as they are for other second-half picks.
In your case IIRC, that would mean you could trade Jason Kidd for any other second-half pick or combination of picks, but that would not apply to KD, Russell, Pippen, Klay, or Ray Allen (though they could still be traded for players of the same era).
