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A Bit Late For Contentment In Skyrim

This latest Skyrim character that was created from yesterday's angst isn't so bad.  Heavy-armor, one-handed, blocking, with a bit of conjuration on the side.  Straightforward, perhaps, but he gels well the idea of dragon shouts because he has no spells interfering with it.  He does not do much sneaking but, you know, I can still lurk fairly effectively if I want to try to eavesdrop on my enemies before bashing their skulls in.  I've been playing on "Expert" difficulty, and I feel reasonably well challenged... but then, I've yet to abuse end-game smithed and enchanted gear fully.
Gerland Swaine, pretty straightforward Skyrim warrior, albeit
with a bit of conjuration on the side.
Granted, even though I got level 19 with him (from level 1!) in one day, I know I won't be able to complete everything I wanted to complete about Skyrim before Monday.  So it's a bit late for contentment, I might as well accept that as long as I enjoyed the journey, I suppose rolling a ton of alternate characters was worth it

Thus relaxed, I'm pondering to myself that maybe I aught to change the way I play the game.  I've had this goal of, "Complete as much of the content in the game as possible with one character."  I'm thinking I should change that goal.  Instead, I can have multiple characters, but each character only completes one of the major guilds in the game.  In other words, each Dovakiin can only be the head of the Companions, the Thieves' Guild, the Dark Brotherhood, or the College of Winterhold.

This essentially leaves me with four separate character concepts to pursue as I feel the need:
  • The Companions character: warrior-tree focused, probably a character similar to the way Gerald Swaine (mentioned above) is built: heavy armor, a melee weapon (perhaps I thought make a stormcloak alt with two-handed instead) and block.  Given the proximity to The Companions, he's an optimal character to pursue the traits of a werewolf, but he'll still side with the Dawnguard if they let him.
  • The Thieves Guild character: thief-tree focused, more focus on mercantile skills (such as speech, lockpicking, pickpocketing), probably will do lots of dispatching foes with archery because he's not suited to fighting up close.  My youngest (level-wise, 6) character is currently here, and will continue to invest in archery, stealth, and light armor perks to continue along these lines.  Built to be a sneaky thief, he'll be able to get in, burgle whatever, and get out without being spotted.
  • The Dark Brotherhood character: thief-tree focused, less focus on mercantile skills, more focus on sneak attacks (15x dagger sneak attack damage perk mandatory), probably make him dual-wield in combat, and go heavier on the alchemy (for a plethora of poisons).  I have a dagger-focused character who will work well here.  Built to be an assassin, he'll be able to get in, kill a target, and get out without being spotted.   Seeing how he's such a heartless murderer, it makes sense he could be the vampire of my characters, and side with them during the Dawnguard expansion. 
  • The College of Winterhold character: mage-tree focused, unarmored.  Focusing all five spell schools would be awkward, I'll probably focus him mostly on illusion, conjuration, and destruction.  Floyd The Indirect is a good point to pick up here, only really lacking on the Destruction front, but that's pretty much just a channel for mana-to-enemy-hitpoint-removal once the battle is already going favorably for him.  A wizard's focus on acquiring arcane knowledge to make lots of uber magic is pretty much all he needs to worry about. 
  • All other quest lines remain viable regardless of your choice of major guild.  Other organizations, such as the Bard College and the Blades, have too minor of a quest load to be a concern about doing them as well.  The Civil War arc is reasonably large, but has no bearing on your choice of guild.  The Dawnguard (or their opposition) are essentially an "overtime guild," you can still do that their quests no matter what major guild you pursue.
These are just the overall rules behind each character, and variations are to be expected.  For example, I expect Gerald Swaine, my companions character, could benefit from having a bit of Restoration and Alteration.  All of the characters will likely pursue all trade skills, but some will have greater focus on some rather than others (e.g. the assassin will want to make more poisons, the warrior will want to smith better armor/weapons).  The mentioned skills and perks are just to give them a primary focus, the ones likely to hit the maximum first, allowing them to end combat in their own respective ways.
Before coming to this decision, feeling morose, I found myself wandering Whiterun to
ponder what to do, treating every NPC's quote like it came out of a fortune cookie.
An illogical bit of mysticism, but oddly entertaining, even inadvertently insightful.
Why Condone Alting In Skyrim?

The main reason why I think focusing on four separate characters like this is necessary is because, I'm noticing that, by the time your character is powerful enough to have beat one of the major guild quest lines, character progression is pretty much over.  You'd probably be at about level 30-40 and have your most important skills maxed.  At that point, running off to do other guild quest lines, and advance more (secondary) skills, is sorely vestigial: your character can already handle all the challenges in the game, they don't need more help.  The game itself would seem to be saying, "You've got all the skills you need, so go save the world already!"

A secondary reason for focusing on four separate characters is because it's good for their character concepts.  It's a little hard for the narrative to make sense that my Dovakiin is the leader of the noble ruffians in the companions, the greedy-yet-relatively-bloodshed-avoiding career criminals of the Thieves Guild, the murderous cult that is the Dark Brotherhood, and the eccentric mages of the College of Winterhold.  I'm pretty sure The Companions would not like to hear their honorable harbinger is performing petty crimes for the Thieves Guild, nor would the stuffy academics of The College Of Winterhold like to hear that their archmage has a second life of murdering people for money in service of the Dark Brotherhood.  It's very conflicting, not unlike being a polygamist with multiple households, I'd have to spin that I'm deceiving someone to make all four guilds work, and I find it hard to believe I could be a famous guild master and still pull that off.

With the load of things in my Dovakiins' "to do" list shortened considerably, hopefully I'll be able to make some progress where I did not before.  So far, across all my characters that I have ever made, I have only completed the College of Winterhold line.  Twice.  I'm about half-way through The Companions, a quarter way through the Thieves Guild quest, and barely even joined the Dark Brotherhood.  Yes, there's a bit of skill overlap between a Thieves Guild character and a Dark Brotherhood character, and I might just make an exception to the "complete one major guild quest line per character" goal, but I've isolated a few reasons here not to.
Yesterday's comments about the importance of toe-to-toe fighting are still a concern.
Here, I managed to pull a giant all the way to Bleak Falls Barrow from the valley on the
other side.  It took a few reloads, but the giant killed the bandits guarding the entrance for me
and conveniently got itself wedged on a ledge where I finished it off, all at level 6.  The
point is that I'm far too good at exploiting fighting at range to not trivialize the challenge.
This multiple character solution is not without a potential difficulty, as it's rather tricky to switch between characters.  It'll likely need to be done whenever I'm bored of the current character I'm playing.  However, if it's done too often, it's rather easy to feel disoriented.  The quest journal will be of some help, as it not only tracks quests to do but quests already completed, and just a cursory glance is all it takes to remind me where I am.  Ideally, I would want to avoid switching so very often that I don't feel immersed in the current character I play when I play them.

With any luck, I will no longer need to start over.  When you stop rolling new characters, yet continue playing the game, completion is inevitable, merely a matter of time.  Yet, the possibility exists I could find myself dissatisfied with all my characters, and what then?
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