We have a thread about equestrian technology, I think. What strikes me the most is their kitchens. They're very, very modern. I'd have to rewatch the episode with the cupcakes song, but I'm pretty sure Pinkie have all the modern conveniences like fridges and stoves. The biggest problem I would see isn't the monsters, the lack of women ( ... ) or the food - you can live on a vegetarian diet, monsters seem to be limited to remote locations (and Ponyville is actually quite close to the Everfree, really) so I guess you could live all your life in safer parts of Equestria without ever having to worry about it (or go live in Australia for a few months before moving to Equestria ). The biggest problem I see is being a biped in a world populated with races who have a very different morphology. Will you find a bed that fits you ? We have no idea what's the size of a pony compared to a human's. Will you bump your head on every doorframe, like Gandalf visiting hobbits ? How many things would you have to custom-build to suit you, and how much money will it cost ? And, most importantly, will the doctors be able to heal you, should something serious happen to your health ? There's a lot of stuff that look awkward for ponies and better suited for humans though. So maybe you'll fit in fine, with only annoying details popping in here and there.