Knuckling Down and Bringing Things to Order

Alright, every time I try to sit down and write the next chapter, I find myself re-reading what I wrote last, wondering why I was taking things in that direction, and rewrite it all to take things in a completely different direction. As you can imagine, this was getting more and more frustrating and taking more and more time as I had to juggle more and more plot points and character progressions, and I finally got to the point where I rewrote the same thing several times, making no actual progress. This wasn't a problem in previous chapters because I could afford to 'wing it', but now I need to stick to specific benchmarks and do so believably.

So, I'm making an outline. A timeline, specifically, so I can have a general idea of what he's doing and why, as we travel down the memory lane of Equestria's most evil tyrant.

I hope that, by doing this, I don't write myself into a corner and get frustrated again, and have some more clear direction in where I want to take this. It would also help if I only did one edit when I finish the chapter, rather than constantly knocking everything down and trying to build it back up and continue from there... Ah well.

Some help would be appreciated. Namely, I want someone to go over the timeline I'm constructing and see if there are any inconsistencies. I'm not so concerned with violating canon; I already know one point where that's been violated, namely with Celestia and Luna being in Canterlot Castle already when that was founded AFTER Nightmare Moon was banished. I'm much more concerned with internal consistency and believability. There's certainly a major area where I'm pretty darn sure I'm going to be violating canon (but in a good way that reasonably fits the evidence!), and with the Sombra storyline coming out int he comics, there will almost certainly be others. Unless I'm prognosticating in my writing and I'm NOT actually violating canon, which would be awesome, as I could tell everyone "I TOLD YOU SO!" and I'd become some sort of Brony Prophet. But most likely not.

Bear in mind, if you do want to help me, SOME MAJOR PLOT POINTS WILL BE SPOILED. I don't wanna do it, but I don't see much of a choice; you can't test the internal consistency without knowing what is being tested. I would also ask that you promise not to spoil it for anyone else, but that's a given.