I also been replaying Skyrim of late after long time. I had previously played:
- Warrior, 1 handed+shield, very tanky all in all. I played this on launch, 95% unmodded and min maxed it to hell. Got bored very fast.
- Mage, run of the mill destruction focused glass cannon.
- Rogue / Archer, focus in avoiding melee
This time I went with a class which would focus on the skills I found most fun, I ended up with a sneaky magic using assassin/thief. Something along the lines of Letho from Witcher 2. Stealth isn't perfect in the game, but it is way more fun than rushing in tank-style head first into every encounter, and can be made better via mods. I also think one should not do all quest storylines, but those that suit the character. For example, my dude finished thieve's guild and dark brotherhood, but I ain't planning on doing the Companions.
The biggest problem was getting stuck to routines and min maxing. Min maxing is dealth with single decision: completely skip enchanting and smithing, makes loot meaningful once again! Routines can be battled with mods such as Random Encounter Zones and replacing old loot with new, such as Immersive Weapons and Immersive Armors. Skyrim ReDone makes leveling fresh experience again and Interesting NPCs adds some life (and additional voice acting) to the world.
Someone already mentioned it, but I also encourage not dumping all the skill points to one tree, but rather spreading 'em around. For example, my sneaky assassin uses illusion spells constantly, but I've yet to invest a single point to the tree. This playstyle of using many skills also means I have favorited million of them, managing them with Categorised Favorites Menu makes life easier.
Also, avoid fast travel. I completely refrained from using it for first ten hrs or so of this char, and discovered new locations and encounters I had missed before. Try to make traveling fun, just avoid clicking yourself around the map. For example, Convenient Horses makes horsing around much more fun (can tell your followers to use horses and horse armor[!]). Lately I've been using Haste spell from Midas Magic to zip around, Skyrim ReDone also add reduce gravity and walk on water spells, which combo quite well with it.
Some of my favorite mods:
Midas Magic: Good spell collection, although some are clearly OP (force push esp.), I just avoid using them. Has a clever spell acquisition system of having to craft spell books using various materials.
Psychosteve's Dragon Priest Masks: Jus
Guard Dialogue Overhaul: Less of mocking queries of misplaced sweetrolls.
Ethereal Elven Overhaul: I won't touch the issue of graphical changes too much. Everyone has their own taste regarding the cleanliness of faces, and that's cool. But personally I prefer my elves looking bit more like elves than sinister aliens.
Acquisitive Soul Gems: No more petty souls in Grand Soul Gems! Hooray!
Project Reality - Climates of Tamriel - Weather - Lighting: I know! I said no more graphics mods, but just this one. Mainly because it makes nights darker, so you have to plan your traveling accordingly. Has several levels of darkness option during installation.
Install and manage mods with Nexus Mod Manager and optimise the load order with BOSS. Fun playthrough also consists of browsing, installing and uninstalling mods during the playthrough, so get out there and keep discovering cool mods! Skyrim Gems is a good mod compilation site, used it myself to find the majority of mods for this playthrough. Just remember that you can mess up your game with too many mods, if the memory leak issue happens, so keep an eye on your savefile. It should never go above 20 megs.
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