Don't you think it would add a lot to the game to be able to play a more evil side? What if you could make your own fake money(forgery) to buy stuff with rather than working for it, and then avoiding the legion, competitive bandits, and 'good Samaritans' with axes. Or even like pirating or smuggling. I'm not sure if boats(that are usable) are confirmed or not, but wouldn't it be awesome to smuggle around stolen goods or Skooma? Just organized crime in general(besides the thieves guild- they have feelings for some unknown reason) seems like something that a lot could be done with and would be a lot of fun. You could actually be evil when stealing something- not just playing the petty thief or 'Robin Hood' thieves guild.
Tell me what you think, DISCUSS!!!!

Sure I'd enjoy it.

It'd be cool if you could engage in trade/smuggling operations for profit. You'd go to a store, get a donkey + cart + goods and have to escort it from that store to another store that would buy said goods. It'd be like Freelancer in TES

I don't know what kind of goods you'd smuggle besides drugs and maybe necromancy stuff. Skyrim seems to be a fairly 'small government' place so it's not likely they'd have an embargo on weapons or magic or whatever.

I'd love to be able to play as different roles fluently throughout my playthroughs. Unfortunately, I highly doubt this will make the cut even in future games down the road. Spears are a problem. This idea is beyond that.

It would be great to have a lot of that going on. There's so much to do with the thieves guild if they break that robin hood trend that you mentioned.

You can get smuggled stuff cheaper though- depending on what it is. So it could be just every day items, but it would make for some really fun quests