How would one do this? (rewatching spice and wolf ad it inspired me)

Everything into speech i guess. But i wouldn't really use any combat i guess, maybe a dagger only.

Oi i wish there were carriages i could ride around, like red dead redemption for example.

I'm doing this atm on my Wood Elf Boris. Everything into non-combat thieving skills except for Archery.

I don't even use Enchanting because I don't want to be an expert in combat, I sell all of the enchanted gear I come across. Which makes me very rich when coupled with the perks in Speech.

interesting, though im afraid ill get bored with nothing to spend my money on. I'm very goal oriented. (once i hit my goal i normally become sad and bored)

I'm working on a build that would make you spend money. It isn't quite finished yet though..

I'm roleplaying so I'm not really searching for a goal. I agree that there isn't much to spend money on in Skyrim. Look out for a wacky thread coming soon detailing the build that I'm currently making. Some people are going to absolutely despise it.

Also note that Lockpicking has some really cool perks that drastically increase the amount of loot you find.

heh good idea, ive never used thoose perks before.