I would do what needs to be done.........kill the rebel scum!

Abuse alchemy, become the richest person ever.

This question may be quite hard to answer fully but here goes - to what extent is it possible (generally speaking) to live a life as the above examples describe? Or are most of them actually not really possible to any great extent?
Has anyone gotten into one of the live-styles mentioned above, to the many details it describes ?

I'd be one of the many terrible bards.

I'd probably be a part of the College of Winterhold to get a good grip around magic. Would probably move Windhelm and settle there as a worker or sellsword

I noticed a lot of people are eager to say they'd basically do the same as they would in game. I admire your balls.

Me, I don't think I'd appreciate risking death daily. I think I'd want to be a blacksmith somewhere. I quite like it in Ivarstead so perhaps there.

As for alignment, (if were on the D&D alignment chart) I'd probably be Lawful Neutral.

I'd still be with the Thieves guild, extorting and stealing with my fellow Guild brothers and sisters.