Say I am watching the 11PM news “from recording, from the beginning” at 11:15PM.
Is there a way for it to start recording the channel live so when the news is over it automatically starts playing Colbert, even if Colbert wasn’t set to record?
No. You have to tell it to record the next program. (No offense, but the software can't read your mind; how will it know you want to record the next program—which is not scheduled to be recorded—unless you tell it so?)
Maybe I'm not understanding your request, but why should it have to start recording, if what you're asking for, is for it to simply start playing live, after the show you're watching has ended?
YouTube tv does this, yes I know it works differently.
Maybe I'm not understanding your request, but why should it have to start recording, if what you're asking for, is for it to simply start playing live, after the show you're watching has ended?
I want it to roll into the next show like I hadn’t been watching a recording, but had been watching live and paused for 20m.
If you paused the live program, then the live feed will continue. It does not stop after a program segment, but continues indefinitely. That is the nature of linear programming. Program segments are merely markers along the infinite stream.
(Has the world really devolved to the point where on-demand is de facto and the concept of live linear programming is foreign ...)
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Just bring up Channels on a different device and click record. 
Assuming you're watching the recording of the news , you could go into Adjust Recording options, and set it to end 90 minutes after end. Continue watching your recorded News episode and it'll bleed over into Colbert afterwards.
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Yes, we went digital and lost the ability to sync time(sloppy design?). Try watching the same "live" program on multiple TVs and see if things are in sync across multiple screens 