Oblivion:Roleplaying/Gray Fox

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Become the most wanted thief in Cyrodiil

After the end of the Thieves Guild quests, you become the Gray Fox which is a great roleplaying opportunity.
Wear full leather armor and if you can, enchant it with good enchantments for a thief (Fortify Sneak, Chameleon etc).
Live in the Guildmaster's Quarters and show off the best stuff you've stolen there.
Never take the Gray Cowl of Nocturnal off around anybody that isn't in the thieves guild.
Since the curse has been lifted, you can live another life besides the Gray Fox which means that you can try to keep up two identities.
Steal from only the most challenging places (Castles, Nobles' Houses)
If caught by guards wearing the Cowl try to escape or maybe even fight them to the death.
Never steal anything without wearing the Cowl.
Don't use the cheating method of stealing something in clear view then taking the cowl off.
Complete Nocturnal's quest to receive the Skeleton Key so you possess both her artifacts.