I'm by far the most comfortable with Skyrim, simply because it's the fucking north. Cyrodil is alright, but far too warm for me. High Rock is decent but suffers a similar problem as Cyrodil. Morrowind is decent, especially Solstheim, but I can't deal with all their freaky jungle shit. Flying Jellyfish? Fuck that shit. Giants I can bear, but Flying Jellyfish farms and Giant Flea buses are absolutely innegotiable, nonacceptable, and out of the question.
For race I'd have to say either Nord or Altmer, with Khajiit and Argonian tied for third.
Nord because they're basically humans, like me, but unlike the Imperials (and even Bretons) they aren't from the equivilant of hot, shitty places on Earth. I'm glaring at you, Italy and Greece.
Altmer because I feel like if I was taken into TES and made one of their races based on my own stats, I'd probably be an Altmer, albeit on the low end of the "I'm a total douchebag" scale.
Khajiit I'd be cool to chill with because I feel like they could give a fuck less about Skyrim's Politics, just like me! Also the whole being nomadic thing really jives well with me.
Argonians are also pretty alright cause I really like the world view their whole fucking race seems to share, which as far as I can tell (or remember) seems to be "don't be a dick".
Oh and I guess Blackscales are pretty cool too, even if they are filthy fucking rogues <.<