It's a nightmare to track and essentially is a slippery slope (speaking from experience). We had it for a while, but ended up getting rid of it and instituting a rule that all trades are final at the time they are executed.
For example, in your scenario "For Example: 2nd Rounder if PLAYER X totals < 200 points by end of season; 1st Rounder if > 200 points", the team giving up the pick now can not trade their 1st or 2nd round pick, and as commish I need to track that. But, the team receiving that pick could then conditionally trade the pick they may receive in a deal where if it's a 2nd round pick, I deal it, if it is conveyed as a 1st round pick, I deal something else.
We also ran into a scenario where a deal was for the "earliest" 2nd round pick a team had (they had multiple at time of executing the deal). Draft order determined by season end finish, so this would happen after the season was over. As season progressed and it became clear one of those picks would be very early in the round and more valuable, they then dealt that pick in a different deal, so that they would be conveying their only remaining 2nd round pick to complete their prior deal. Technically no rules against that, but the receiving owner was pissed claiming that their deal was for the earliest of the picks he had at the time they executed the deal and that he could not trade that other pick as it was tied up as a "conditional" part of their trade.
As a commish, it was a complete nightmare. It was definitely fun to try and negotiate deals with contingencies, but it just was not practical to keep as part of the league, thus the decision that all trades need to be "final" when executed, no further contingencies.