Need Opinion on Exploring the Castle Sequel Idea

I've been having a lot of trouble with trying to come up with the plot, as fun as writing Exploring the Castle was, I don't think I can pull of another story like it unless I made it have only one ending. I want that to be a defining point in the AU as a whole, I'm not sure what it would be exactly, but I want it to have significance.

However, while The Toppats and Mist Veil are making a name for themselves, Henry would have to be doing something, and I don't want to keep him to just cameo appearances. Thus, I'm going to write a fanfiction in the same vein as a Tumblr Ask Blog, Henry has left Canterlot and the readers can interact with him and The All-Knowing-Author-Insert from the fail flavor text, ask questions and the like. Henry will start near Ponyville and make his way to Manehatten.

Henry Stickmin escaped Canterlot, low on funds he wandered across the Equestrian countryside, and somehow made it Ponyville. With too much time on his hands between doing odd jobs around town, Henry posts the address of a post office box in the morning newspaper, and waits to see what he'll get in the mail.

A week later he gets his first letter.

What are your thoughts? Should I go through with this story idea?

Comments

[jimerjam]

trapped in tartarus?

[Dragonfire2lm]

5404696
Henry hasn't really done anything bad enough to warrant a trip to Tartarus. Cool idea though.

But I was asking if the idea presented in the blog was something readers would be interested in.

[jimerjam]

5404817
it can be argued/skewed that he
literally attempted to steal the elements of harmony

[Dragonfire2lm]

5404991
That would mean there's a definitive canon ending, which goes against the open-ended nature of Exploring the Castle. Henry could maybe end up in Tartarus later on but I don't really see the series heading in that direction.

I'm looking for advice on whether the idea I presented in the blog would be something readers would be interested in.

[jimerjam]

I think it would be interesting,
maybe gilda hires him to steal/find the idol of boreas

[Dragonfire2lm]

5405009
Maybe.