TWOW Season 2 is an upcoming TWOW season which will be fully automated.
In TWOW 14B, the amount of people on the discord was 702. Cary asked if all of them were going to join S2. If this was true, there would be at least 702 contestants ( + more ) that would be in TWOW.
Although this is a good number (being close to 1,000), it wouldn't be manageable using YouTube PMs due to their system not being perfect. Discord PM may be better, but it's still around 700 PMS. This means that Carykh will have to find an efficient (but not too efficient) method to get PMs.
This has changed to nearly 2000.
Cary has mentioned that the second season of TWOW would operate on it's own website and be more automated than TWOW S1, allowing TWOWs of other languages to operate.