I was thinking...

Bosmer: sneak, daggers/one handed, alchemy, light armor, speech (?), and maybe a stealth enchanted ring?

Just curious. Haven't tried it.

Someone has to have...

I might RP a hobbit in LOTR online, but most definetely not in Tamriel. Oh, and Bosmers aren't that small or harmless. Try reading "A dance in fire" sometime.

As a LOTR fan, I think that would be interesting, but I think a hobbit would much prefer to stay in their cozy homes, farming, drinking ale, smoking pipe weed, rather than go out on adventures (unless you're talking about Bilbo or Frodo)
(And the height of the characters in Skyrim won't probably help with RP-ing as a little creature like the hobbits... ) But you could try and tell us how it goes!

I wouldn't in TES because they don't exist, any more than I would RP a race car driver.

BUT, if I were going to do it, I would use Breton as the template. They look the part far better. TES elves just look too alien and freakish, and hobbits just look like happy fat little humans with no shoes. (Make sure to never wear shoes.)

I hope you're on PC! Don't forget to use the setscale console command! This will change your character size. I know that setscale 1 is for a normal sized character, so try setscale .5 and see what happens.

Sure, and I play a Bosmer so I know your right, but sometimes after you've made a few "serious" characters its cool to just screw around a little and have some fun.

I made a "Native American" Redgaurd in Oblivion that was a kick in the pants. (long hair, war axe, marksman, and fur armor) He just rode around hunting and raiding Imperial settlements. (of course I had the right music too)

I also made a blue(ish) faced bosmer that I called Dwarven as well.

edit: And of course they don't belong in TES, but its a fantasy world so I feel free to fantasize just for fun.