"The starting city? r u a plebe!" - Some annoying guy.
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"I like Whiterun. Balgruuf is the nicest, most level-headed Jarl I've met. Even if his name sounds a little... unfortunate." - Ayumi
I think Whiterun is the jewel of Skyrim. Sure it's a little small for being a major trading hub, but it's a nice place.
Plus Balgruuf is practically the only Jarl to treat the Dragonborn with any real respect. And he's Ballin'. (SWAG!)
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Oh well, doesn't matter. I'm Jarl Ballin' Ballin' Jarl Ballin'. SWAG!
...I watch way too much of mans1ay3rs' work. But it's just so good.
Here, let Balgruff educate you.