Yes, Obama did this
https://obamawhitehouse.archives.gov/the-press-office/2017/0...Which completely irrelevant, because of this https://www.whitehouse.gov/the-press-office/2017/02/10/provi...
I'm not sure which order your first point is in reference to, but please point it out - https://obamawhitehouse.archives.gov/briefing-room/president... - none of this is a secret.
The bigger point is that you seem not to know how to process the fact that Obama issued a lot of EOs on his way out. Process this by understanding that he did not invent the "midnight regulation." I, like you, also believe that Obama's an incredibly smart man, but I do not grant him literal prescience in predicting the actions of the Trump administration in the recent weeks.