I'll just jot down some of my thoughts and you can comment on them as we go, hopefully after a bit we'll have a good idea of perk distribution and everything else for your build. I'm sure others will add comments as well. Here are some skills you may be interested in leveling, you can just reply back with your intentions for each. [*]Lockpicking - general thief skill. [*]Pickpocket - general thief skill. [*]Heavy/Light Armor? - One is inevitable. Since you'll likely be able to max the armor rating on all sets eventually which you choose will largely be up to what you think looks better. [*]Enchanting - This is easily the most powerful skill in the game, and will allow you to enchant your armor/weapons to customize them to your build. However, I'm not sure if investing heavily into it breaks the role-playing aspect of having a thief/assassin in your mind. [*]Smithing - Useful if you want the better armor earlier or want to improve them as much as possible. Same role-playing caveat as Enchanting. [*]Archery - Like you stated, you'll want to max this. As far as point distribution, it really depends on whether or not you want to use magic often. If you're never going to use Destruction, you may be better off not putting any points into it and just dumping them all in stamina/health. If you max enchanting, you can always enchant 1 set of armor to get 0 spell cost in two schools of magic anyway, but that will take awhile and will hinder your magic use in the beginning (again, if you intend to use it).