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Techy Cutie Pony Collection!

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Squirmy Hooves
The End wasn't The End - Found a new home after the great exodus of 2012

Actually, Cherry Berry is the one that has it as a rental. (Notice it has her color scheme) Pinkie Pie usually pulls out an identical one from the hammerspace in her… uhm.. womanhole, and has an unlimited supply of these. And the merchandise has it belong to Twilight because it makes more money.
JJII
Non-Fungible Trixie -

Crazy Theory Time: Everyone with a Hot Air balloon gets it from the same place, said place only sells one type of balloon. You should be able to figure out the rest.
Squirmy Hooves
The End wasn't The End - Found a new home after the great exodus of 2012

Actually, it is owned by Cherry Berry as a rental, but as the only balloon in town, is often used by Pinkie Pie. The name “Twilight Sparkle s’ Twinkling Balloon” comes from the factory that makes the balloons: “Twilight Sparkles (tm)” and “Twinkling” is just the model type. Our sweet dear Twilight Sparkle was just named after the same book character as the balloon factory.
Rainbow Dude
The End wasn't The End - Found a new home after the great exodus of 2012

@BP  
Yes, it was her on The Mysterious Mare-Do-Well. Great to see some subtle continuity, with Cherry Berry being a balloonist, even with that hat.
Background Pony #8191
Wasn’t she the one about to crash in The Mysterious Mare Do Well or was that another pony?
Background Pony #8F4D
“Go pick up my laundry, Cherry. Carry these cakes, Cherry. Take Twilight’s balloon back to town, Cherry. I don’t get paid enough for this shit.”