How far back acloudyskye's world goes
Genius shows acloudyskye's first song to be Runaway, dating back to October 14, 2017.
The first time Enth shows up is in Spaces, from December 31, 2017. Enth doesn't show up again until Parting Gift (April 15, 2018), then starts consistently appearing in When There Were Others (August 4, 2018) and onwards.
As for videos: the first one at all is At Rest (February 15, 2021), and FIRST ENCOUNTERS doesn't start until March 5, 2022.