After having spent 100's of hours with my evil Battlemage Arialthalis I am now going to try playing as a stealth character, an assassin, yet I have not played one in literally years and I need help with roleplaying as one. Any help with this would be appreciated (I do not mean eat food, sleep reguarly, do not fast travel etc. I mean backstory, activities I could do as my character etc).

My character is a Mystic Elf (from a mod) male and is middle aged if that helps. I have currently decided to use Blade, Marksman, Light Armour, Sneak and Illusion, unsure on the other 2 skills so some advice there would be appreciated.

Thanks in advance for any advice

Alchemy and security/athletics

aswell as following the DB questline..

pick random characters to assassinate... ie search a random NPC on uesp and assassinate that person for whatever reason you see fit.

or pick a certain race.. ie argonians murdered your family and you kill any argonian you get the chance hostile or not.

same as above but with imperials.. imperial colonists destroyed your village to build a fort and now you take revenge whenever you can.

A great was to find characters to assassinate for just plain fun or if they have a shiny new weapon you want, is use a mod. I use T.I.E which contains npc's from Tamriel Traverler's and a few other things I think, but they are everywhere. I find them in town walking around, around settlements, and a few walking the roads. T.I.E also disables the leveled item list so many of the npc's have nice items that you might otherwise not find in game.