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This used to be my headcanon during season two explaining why twilight sparkle and her family seemed to be rich ROFL

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The problem with their technique is everyone that knows anything about them is either too scared or too dead to talk, so they never manage to develop a reputation and most of Equestria still thinks they’re just a bunch of dorks.
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@Ferrotter  
I don’t know it would be right to call it a “home” she had in canterlot. really we only ever saw a single, albeit very large, room at the top of a tower. It could very well be a condominium or highclass apartment or something of the sort.
Ferrotter
The End wasn't The End - Found a new home after the great exodus of 2012

@Spiritus Arcane  
I agree, it’s just short of stated canon. They’re Canterlot native unicorns; Twilight’s foalsitter was a princess; (and apparently her brother was not only Captain of the Guard, but eligible to marry said princess); she was personally tutored by the ruler of their entire land; they apparently have enough bits and/or clout that they could buy Twilight her own private (and rather spacious) home in Canterlot while she was in school; and she could afford to leave that home unoccupied indefinitely without giving it a second thought while she spent likely several years living in another home Ponyville. Arguably Twilight’s parents may also have had something to do with getting her a second private home in Ponyville’s municipal library, though it’s just as possible Celestia arranged that particular home for her.
 
Not to mention, her neighborhood in Canterlot was clearly good enough that her house wasn’t burglarized despite being obviously unoccupied over a span of years. Though it’s possible that just isn’t a consideration in Equestria generally; they do seem to have police, but they seem to be more involved in keeping general order than actually stopping crime. The ponies clearly understand the concept of crime, and believe it could happen at least in theory, but other than some (entirely mutual) vandalism of desserts on the train to Canterlot, the mistaken belief that Troubleshoes was a saboteur rather than a well-meaning klutz, one reckless endangerment via tornado (handled via military rather than civilian justice), and one attempt to frame Rainbow Dash (ditto), there really hasn’t been any particular crime shown to occur in Equestria, ever. And no actual theft. Among the Dragons (including Spike, once), the Diamond Dogs, and the Amarimaspi and Griffons, yes, but not among Ponies. But assuming the complete lack of theft among ponies isn’t the sole explanation, Twilight’s abandoned home in Canterlot had to be in a pretty upscale area to be undisturbed for so long after Twilight abandoned it.
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