*perfect build (no mistakes with leveling always +5 +5 +1)
*no quests ruined (no npc killing that I may need for a quest later even if it's just a side-quest)
*collecting a complete set of weapons and armour, (a collection in it's own right) for it, stored in my house.
so for me it's mostly about thinking about what I want to become statwise as a level 40, and make sure I pick race, birthsign, atributes and skills to suit it.
also I need to watch my leveling, pick skills that level not to much as mayors so I can manage the +5 boosts
for quests I use the wiki.. if I am thinking about killing an npc I always check if he/she is needed in a quest later BEFORE making that kill.
about the collecting gear, that takes little effort, just maintaining a sheat what I already have.. so I wont use up valueble inventory space for items I already have in my set.
(as it is impossible to remember it all on my own)
and when I feel something is missing for my char, anything, I try to downloand or make a mod, to fill that gap.