I'm about to do another replay of Oblivion while gearing up for Skyrim, any thoughts for a race/class/specialties to spice up this playthrough. Thanks for your input.

Race: Imperial
Specialization: Stealth
Class: Assassin
Skills: Alchemy, Acrobatics, Blade, Light Armor, Marksman, Security, Sneak.

Assassins, Rogues or any type of stealth characters are quite fun from my experience. Alchemy is great, and can be quite a valuable skill once you level it up a bit and collect the right reagents, while you also have a mix of close and long ranged combat. I've made multiple characters since coming back to Oblivion, but it really depends on your preferences.

What sort of character are you going for?
Do you want some Magic?
Do you want a Heavy Melee character?

Character development has been changed as well; "class" selection and "attributes" selection are no longer used, and instead of the twenty-one skills in Oblivion (twenty-seven in Morrowind), Skyrim will feature eighteen skills. Removed skills with no singularly defined skill replacement include Blade (shifted to other combat skills), Blunt (also shifted to other combat skills), Hand to Hand, Mysticism (spells shifted to other magic skills), Athletics, Acrobatics, and Mercantile (merged with another skill). The confirmed eighteen skills are Illusion, Conjuration, Destruction, Restoration, Alteration, Enchanting, Smithing, Heavy Armor, Block, Two-handed, One-handed, Archery, Light Armor, Sneak, Lockpicking, Pickpocket, Speech, and Alchemy. Faster player level increases can be achieved by increasing developed skills.

this is from the wiki so it will come in handy

The polar opposite of what you played last time :wink_smile:

Dude be a Bosmer, thief sign, an custom class. Only work on his dirty bow skills an destruction magic. Be a sneaky adventurer assassin thief! B)