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This is something I'd been thinking about since watching Fantastic Beasts and Where to Find Them. And yes, I'll be doing this in a Railfan Brony video. Copied over from one of my posts on SiF's POSTOPIA thread, here is my intereptation on how the Steam Team could be sorted into the four Hogwarts Houses. Here are their respective traits:

Gryffindor - Bravery, nerve, chivalry, courage, daring
Hufflepuff - Dedication, hard work, fair play, patience, kindness, tolerance, unafraid of toil, loyalty
Ravenclaw - Intelligence, wit, wisdom, creativity, originality, individuality, acceptance
Slytherin - Resourcefulness, cunning, ambition, determination, self-preservation, fraternity, cleverness

The Gryffindors
Thomas - It's pretty obvious, isn't it?
Gordon - His boastfulness could add to how the other three Houses would think negatively about Gryffindor - he's brash and often fights with other engines. In fairness, he also has some Slytherin qualities to him, especially when it comes to pulling certain trains.
Donald - He's got a certain charisma about him, and the fact that he had the courage to rescue his brother from scrap definitely puts Donald in Gryffindor, with a dash of Ravenclaw.
Emily - She's a bit tricky to pinpoint; some would view her as a Hufflepuff and call it a day, but as much as I'd love to put Emily in my House, I think she's more of a Gryffindor if you consider her actions in Emily's New Coaches and Best Engine Ever. The fact she was often portrayed as overconfident during seasons 8-12 could also add to the negative traits of Gryffindor. But in the end, Emily could still be a Hufflepuff at heart.
The Ravenclaws
Edward - Some of the bigger engines (usually Gordon) do look down upon him, and they'd probably consider him an old iron Hufflepuff, but don't let his age fool you. He's saved James from a runaway and got his passengers home despite being crippled, which could put him in Gryffindor, but in the end, Edward is a Ravenclaw, through and through.
Toby - He's the voice of reason in the Ffarquhar trio, so Ravenclaw works best for our resident tram engine. I will also say that Toby's dedication to Henrietta is very Hufflepuff.
The Hufflepuffs
Henry - Of the mainline trio, Henry is often viewed as the nice one. He does care about doing a good job to please the Fat Controller, so he fits well as a loyal Hufflepuff. And considering his love for the forest, he'd make an excellent Herbology student under Professor Sprout.
Percy - Like several others in the Steam Team, Percy is tricky to pinpoint; he has equal traits from Gryffindor and Hufflepuff. He is brave when he wants to be, but he's also hard-working and dedicated to being really useful, and when he saved James from the rock-slide at the Clay Pits, he did so because it was the right thing and not for glory.
Douglas - He and Donald could be the Thomas equivalent to Fred and George Weasley, but when it comes to sorting Douglas, I'm personally thinking more of loyalty over bravery. He did understand what Oliver was going through when the tank engine was facing the jaws of scrap, and according to the Sorting Hat, a Hufflepuff should never be afraid of toil. Of course, Douglas might also apply to Gryffindor or Ravenclaw.
The Slytherins
James - He's overconfident at times, so Gryffindor is a possibility. However, he'll often do anything to show off his red paint and keep it clean as possible. Besides, isn't self-preservation a Slytherin trait?
Duck - This one could be a bit contentious; most of you would think Duck could end up in Ravenclaw, and I do agree with that sentiment, but I honestly see him more as a Slytherin and should not be interpreted as "evil". They are intelligent and proud (of his GWR heritage), and so if one of Slytherin's traits is shrewd (meaning intelligence), then I think Slytherin works best for Duck - he may as well be the equivalent to Horace Slughorn.
Oliver - Of the Awdry Eleven, Oliver is perhaps the most difficult to sort. When it comes to escaping to Sodor, he did bring Isabel (in the book) and Toad with him. After he was bought and restored, James said Oliver had resource, a Slytherin trait. Though he might have some Gryffindor in him, I feel Slytherin's a good fit for Oliver, a bit like Albus Potter (Harry and Ginny's second son).
Those are my thoughts so far. No matter how you view them as a group - the original seven, the eight famous engines, the Awdry Eleven, the canon Steam Team (eight members), the fanon Steam Team (twelve members) - they all fall into the Houses fairly evenly, so no House is dominant over the other three.

Who do you think could fit which House? Here's some musings from me: (some might not be final)

Gryffindor: Bill and Ben, Stephen, Caitlin, Gator, Samson, Philip, Yong Bao, Rheneas, Duncan
Hufflepuff: BoCo, Mavis, Charlie, Belle, Paxton, Connor, Timothy, Ryan, Peter Sam, Rusty
Ravenclaw: Diesel, Salty, Whiff, Hiro, Porter, Marion, Glynn, Merlin, Skarloey, Victor, Millie
Slytherin: Daisy, Arry and Bert, Diesel 10, Spencer, Dennis, Vinnie, Frieda, Sir Handel

Thomas and Friends (C) Hit Entertainment and Mattel
The Railway Series (C) The Awdry Family
Harry Potter (C) J. K. Rowling

Description
This is something I'd been thinking about since watching Fantastic Beasts and Where to Find Them. And yes, I'll be doing this in a Railfan Brony video. Copied over from one of my posts on SiF's POSTOPIA thread, here is my intereptation on how the Steam Team could be sorted into the four Hogwarts Houses. Here are their respective traits:

Gryffindor - Bravery, nerve, chivalry, courage, daring
Hufflepuff - Dedication, hard work, fair play, patience, kindness, tolerance, unafraid of toil, loyalty
Ravenclaw - Intelligence, wit, wisdom, creativity, originality, individuality, acceptance
Slytherin - Resourcefulness, cunning, ambition, determination, self-preservation, fraternity, cleverness

The Gryffindors
Thomas - It's pretty obvious, isn't it?
Gordon - His boastfulness could add to how the other three Houses would think negatively about Gryffindor - he's brash and often fights with other engines. In fairness, he also has some Slytherin qualities to him, especially when it comes to pulling certain trains.
Donald - He's got a certain charisma about him, and the fact that he had the courage to rescue his brother from scrap definitely puts Donald in Gryffindor, with a dash of Ravenclaw.
Emily - She's a bit tricky to pinpoint; some would view her as a Hufflepuff and call it a day, but as much as I'd love to put Emily in my House, I think she's more of a Gryffindor if you consider her actions in Emily's New Coaches and Best Engine Ever. The fact she was often portrayed as overconfident during seasons 8-12 could also add to the negative traits of Gryffindor. But in the end, Emily could still be a Hufflepuff at heart.
The Ravenclaws
Edward - Some of the bigger engines (usually Gordon) do look down upon him, and they'd probably consider him an old iron Hufflepuff, but don't let his age fool you. He's saved James from a runaway and got his passengers home despite being crippled, which could put him in Gryffindor, but in the end, Edward is a Ravenclaw, through and through.
Toby - He's the voice of reason in the Ffarquhar trio, so Ravenclaw works best for our resident tram engine. I will also say that Toby's dedication to Henrietta is very Hufflepuff.
The Hufflepuffs
Henry - Of the mainline trio, Henry is often viewed as the nice one. He does care about doing a good job to please the Fat Controller, so he fits well as a loyal Hufflepuff. And considering his love for the forest, he'd make an excellent Herbology student under Professor Sprout.
Percy - Like several others in the Steam Team, Percy is tricky to pinpoint; he has equal traits from Gryffindor and Hufflepuff. He is brave when he wants to be, but he's also hard-working and dedicated to being really useful, and when he saved James from the rock-slide at the Clay Pits, he did so because it was the right thing and not for glory.
Douglas - He and Donald could be the Thomas equivalent to Fred and George Weasley, but when it comes to sorting Douglas, I'm personally thinking more of loyalty over bravery. He did understand what Oliver was going through when the tank engine was facing the jaws of scrap, and according to the Sorting Hat, a Hufflepuff should never be afraid of toil. Of course, Douglas might also apply to Gryffindor or Ravenclaw.
The Slytherins
James - He's overconfident at times, so Gryffindor is a possibility. However, he'll often do anything to show off his red paint and keep it clean as possible. Besides, isn't self-preservation a Slytherin trait?
Duck - This one could be a bit contentious; most of you would think Duck could end up in Ravenclaw, and I do agree with that sentiment, but I honestly see him more as a Slytherin and should not be interpreted as "evil". They are intelligent and proud (of his GWR heritage), and so if one of Slytherin's traits is shrewd (meaning intelligence), then I think Slytherin works best for Duck - he may as well be the equivalent to Horace Slughorn.
Oliver - Of the Awdry Eleven, Oliver is perhaps the most difficult to sort. When it comes to escaping to Sodor, he did bring Isabel (in the book) and Toad with him. After he was bought and restored, James said Oliver had resource, a Slytherin trait. Though he might have some Gryffindor in him, I feel Slytherin's a good fit for Oliver, a bit like Albus Potter (Harry and Ginny's second son).
Those are my thoughts so far. No matter how you view them as a group - the original seven, the eight famous engines, the Awdry Eleven, the canon Steam Team (eight members), the fanon Steam Team (twelve members) - they all fall into the Houses fairly evenly, so no House is dominant over the other three.

Who do you think could fit which House? Here's some musings from me: (some might not be final)

Gryffindor: Bill and Ben, Stephen, Caitlin, Gator, Samson, Philip, Yong Bao, Rheneas, Duncan
Hufflepuff: BoCo, Mavis, Charlie, Belle, Paxton, Connor, Timothy, Ryan, Peter Sam, Rusty
Ravenclaw: Diesel, Salty, Whiff, Hiro, Porter, Marion, Glynn, Merlin, Skarloey, Victor, Millie
Slytherin: Daisy, Arry and Bert, Diesel 10, Spencer, Dennis, Vinnie, Frieda, Sir Handel

Thomas and Friends (C) Hit Entertainment and Mattel
The Railway Series (C) The Awdry Family
Harry Potter (C) J. K. Rowling