I did it, I finally finished this huge vector that's been eating away at my time for god knows how long.
I'm pretty happy with the overall result, although there are more than a few things that I'd like to correct due to the screenshot getting so fuzzy at the end I was basically guessing what half the houses looked like.
Critiques are, as always, welcome, but I'd rather they be about how to refine my skills with this sort of thing rather than picking out some of the (many) inaccuracies in the vector. I'd like to improve in the future, as opposed to correcting this for the next month.
Here's the reference for anybody curious: [link]
As well as the higher resolution reference I used for around the town hall: [link]
And here's the Illustrator (AI) file: [link]
As well as the SVG file: [link]
MLP:FIM © Hasbro
Edit: Seems a lot of people are messaging me asking for permission to use this in their various projects. Sorry if I didn't make it clear enough, but I did make this as a resource and you can use it how you like so long as you credit back to me (It'd be nice to tell me where you're using it too, in a note or comment, but that's not necessary).