Shining Armor wasn’t really crazy here. He was just extremely tired.

@Background Pony #F936  
The cause of the ashland future:  

Runs in the family, huh? I suppose their future children’ll be the same.
 
Wait, I just realized that since Twilight Sparkle is now an alicorn just like Cadence, then her baby with Shining Armor will probably be born an alicorn like Flurry Heart. BUT MORE INSANE!! Equestria is doomed.
 
Wait a minute. That’s probably what leads to the Ashland Future.

@Background Pony #140B  
Well we see that and you’re right. But who knows, maybe when she first entered she experienced it as shown in “Magical Mystery Cure” (it was brief, but there was a scene of Twi in magic Kindergarten like in her vision). It could’ve happened in another time we didn’t see, but just starting would make sense. For example in “Newbie Dash”, || We see how she gained her “nickname” Rainbow Crash and how it affected her later in the episode.|| Prior to that, we could’ve assumed that the bullies used it to try to tease her like in “ Sonic Rainboom”. With Twilight, it can also apply on a way that she could’ve been harnessing those bad memories, even though it for get better from what we see in “Amending Fences”.

@Background Pony #7B11  
That her school days were hellishly awful is 100% pure fanon, based on nothing but the fact that fans want everything as dark and angsty as possible.
 
Even before Amending Fences took us inside her school days, we knew she went to Celestia’s School for Gifted Unicorns. Gifted, as in everyone was smart and good at magic just like her. As such, there is no reason to believe that for being smart and good at magic everyone treated her like shit every day. None at all.
 
Why wouldn’t she want to be sent back to magic kindergarten? She’d be the only adult in magic kindergarten! Simple enough.

@Background Pony Number 17  
Well she did have the crippling fear of being late would have her mentor send her back to a place filled with bad memories and childhood trauma, that fear was just made worse when it wasn’t taken serious by those she trusted the most.

To be fair, Shining’s a new father here. What’s Twilight’s excuse?

@Background Pony #FD93  
Shh, you’re ruining a good question :P

@Background Pony #2B0E  
Themselves.

Question: Who gave them their insanity? Their mother or father?