Good analogy.
I do believe the probability of the cliff happening is high- certainly significantly higher than 50%, IMO, but we did just have a pretty decent two recent drafts and our last international signings look pretty good as well, despite the unfortunate loss of Flores.
Our past farm gave us Betts, Bogey, JBJ, Vaz, Beni and Devers. Trading Vets brought us ERod, Kelly & Hembree. Trading prospects like Moncada, Kopech, Margot, Espinoza and others brought us Sale, Kimbrel, Pomeranz, Smith, Thornburg and others. The astounding value of all of these from-the-farm acquired talent far outweighs what we have in the system now. That is clearly undisputable and tangible (not speculative or conceptual). Whether or not the prospects we traded amount to anything or not does not change the fact that we got tangible value from them or for them (via trades).
It's highly unlikely we see anything like this recent influx from our farm value in 2-4 years. Yes, there are other ways to build a team than from major contributions from the farm, but until I see our budget consistently going over $225M or so, I'm guessing we hit a significant rough patch 2-3 years from now. I also see no evidence that DD is a master of rebuilding farm systems with low draft picks and an easier international signing system of the past. Expecting him to do better under more difficult circumstances is not "probable".