The 2018 image shows a single-point switch:
View attachment 721252
So their 'test installation of a dual leaf switch' doesn't have dual leaves?
How long is this "long-term" contract, and when does it expire? From what I've seen, the sole-source procurement contracts are typically 5 years. Even if they are within a 5-year contract, they need to start working on selecting new standards so they're ready by the time they next need to go to procurement. Otherwise they'll have no choice but to extend the current design for yet another 5 years.
The key question here is whether the TTC would seriously allow through speeds to be raised from 10 km/h to 40 km/h or so with the existing switch design if it were connected to a new switch control system. If that is true, then you are correct that we can ignore the fact that we use an expensive and obsolete switch design that only one company makes anymore. But I suspect that regardless of the switch control system, the TTC would insist on a 10 km/h limit through the existing switch design, in which case replacing them with a more modern layout has the potential to save a huge amount of operating expenses over their lifetime thanks to reduced round trip times. So as far as "things we should be spending our money on", it's quite high on the list.