I don't think ornn should have an upgrade for every "key" item in the game. If he gave upgrades to assassin items (like, for instance,
), then it would just be further reinforced to purchase ghostblade as an assassin. Hell, if he just upgraded boots it would make those more necessary than they already are.
AD and AP assassins are more intended towards mid game, when defensive items haven't been purchased by fragile targets, and while shields and healing aren't going to instantly nullify any chances they have. If the target is alone, then fine, they die, that's what an assassin should do, regardless of build type (assuming a serious build, that is).
Right now Rabbadon is just out of favor; AP champions need more power up front during early/mid game rather than power to late game, which is why it often isn't build. That, and they also need durability, because as fast as they can burst a target, they die just as fast. The same applies to AD assassins. They need survivability as well as more upfront power to assist in the mid game, because late game simply isn't catered to them. Black cleaver may not be an option on every AD assassin, but it still is an option. An item that provides 60 AD is still quite useful, especially considering the durability boost it provides, even if they can't make use of the armor shred as well versus squishies it still helps against bruisers and tanks (who can survive initial cooldowns, but can't take the assassin out instantly.)
Certain items must have their niches retained, and Rabbadon's Deathcap is one of those. It must be for an AP power spike at the cost of time and a higher gold price, not another 100 AP item that costs 3000 gold or something. And although not ideal, the black cleaver upgrade can be used on AD assassins, the Rabbadon upgrade can be used on AP assassins, it still very much depends on the player and not just crunching gold into stats, because if that were the case, why would his upgrades matter? They only truly help when you have nothing else to spend gold on.