Recently I started a new playthrough as an Argonian Nightblade, my plan being to become Arch-Mage, Gray Fox, and Listener of the Dark Brotherhood. My issue is that I don't feel like this actually works RP wise. I need some help rationalizing doing this sort of thing, especially having a Noble Lord of Thieves who also worships the void and is deeply focused on furthering Traven's silly war on Necromancy (granted, Mannimarco is a dike). Halp?

I am the same way, even I have an Argonian Nightblade in Morrowind, and he only joins the Mages guild because he thinks that the Thieves Guild is a waste of time, and he is too neutral to be a killing machine to join the Morag Tong, but still he kills people he needs to or has to kill and steals from people if he is poor, and also raids dungeons, tombs ect. But strives to be more skilled in Magic.

But I feel the same way in Oblivion, I'll brb because I had an idea pinned down somewhere so I'll edit this post.

EDIT: Ah ha! I plan to do Oblivion again soon and I am gonna make my Argonian Knight a faithful Divine Crusader (KotN) but keep this in mind too...Backstories!. So here is the dealio (as it worked on my old Argonain guy too):

Farlace joins the Mages guild becuase his bloodline is prominently Magic and to practice his Illusion skills. Fighter's guild because he needs to brush up his melee skills. Thieves guild becuase he needed money BAAAAADLY so he joined, also because his Mage sister was also a thief, who learned after their mother. If things gone bad she went to her hideout (Frostcrag spire). His brother was an DB assassin (who allied with vampires) who shared a hideout (deepscron) who was killled while on a contract that a Morag Tong member also had, so his spirit possessed Farlace so he can clean up the mess and finish up his work in Cyrodiil. SI was a bit tricky because Farlace worships the Divines, so I made it that he went in the gate thinking it was another Oblivion gate, and then kinda snowballs from there, and tries to convert the real sheogorath gave him into a religiously neutral site, where he builds his own "shrine"

I hope I was clear enough, but I made Farlace join all factions with a reason, so if you have anymore questions on the other factions, just ask

It's really hard to justify having a single person become the leader of three different guilds.

Maybe you could never have him/her be the leader of any two guilds at once. Maybe he/she starts out being a petty thief, gets picked up by the Thieves Guild, becomes the Gray Fox, then gives up the Cowl to someone else to pursue a different faction.

Something like that, or maybe someone else will have a better idea. Other than that, I'd say it's better to have that character just go down one path, then make a new character for a different faction, and then a third character for the last faction.

Alright, a much more reconcilable thing:
Mages Guild: Magician
Thieves Guild: Gray Fox
Dark Brotherhood: Eliminator (I'm not going to go to Fort Farragut, ever.)

I edited my 1st post if you didnt notice

One can come up with the mental gymnastics and rationalization to support anything up to and including a combo Divine Crusader / Listener of the DB, but the fact that it feels like it doesn't work is a valuable feeling that is worth listening to.

RP works pretty well with one character joining one guild. Beyond that tends to feel like a player trying to jam a round character into several square holes at once, and at some point perhaps stop being RP and begins to resemble simple 'do-it-all-cuz-I-can' power gaming.

The classic mental gymnastics to jump into disparate guilds generally involves some dark history of (yawn) being abused as a child and watching one's parents suffer at the hands of blah, blah, blah, then vowing to exact revenge and so on and so forth involving one or more psychiatric conditions. . . .

Just my two septims, but honestly, rather than trying make what doesn't feel right work, I would adjust your objectives until it does feel right.

Edit: Oh, I just saw your second post. I think you'll find that might work much better!

DB and Divine Crusader would work becuase http://www.imperial-library.info/content/oblivion-song-pelinal-6

What are the factions Buffy has joined? I'm a big fan of your fan-fic but I've never been quite sure how much was direct fact of your playing.

Buffy has played about 600 hours since April 2009. Her game is not dramatically different than her fan fiction except that in her game she clears lots more non-quest dungeons and plays in lots more waterfalls and travels to visit friends an awful lot.

She has risen to the rank of Journeyman in her guild of mages. That is her guild. She loves both her fellow mages as well as the Arcane University.

She also helped Mazoga, and was rewarded with a big green friend for life, and being dubbed Dame Buffy, Knight Errant of the White Stallion.

She fought in the Arena once to pay for passage home to Bravil after her brief time in prison. Then she fought several more times, challenging herself to face her terror of close range combat in the open. She then quit the Arena, concluding that there are too many foes who want to kill her to continue seeking fights for sport.

She killed that harpy Earana in Chorrol who theatened her and was invited to join the DB. Being an orphan, she was enticed by the lure of the loving family that Lucien promised. When faced with Rufio though, she balked and proclaimed that her killing would not be for hire, so she never joined the DB.

How about your character has multiple personalities? Neither one knows about the others, and they all have unique interests. That'd be one quick fix.

I'm slowly starting to get into this sort of thing and I believe the idea that you should be head of guilds one at a time to be the best solution.

You can also join the other guilds, especially for services and just stay at low ranks. Its like being a part of several clubs in real life. My character has been running the mage recommendation quests because he dreams of the hidden knowledge behind those gates of the tower. At the same time he started to develop a hate for the rich and a soft spot for the poor (Robbin Hood Complex anyone?) and so, has become increasingly interested about the inner workings of the thieves guild, so he decided to join them as well.

Devin has also blocked out a murder in his recent past (killed Mazoga so the lodge is all his now, though this happened before I started thinking seriously about RP, so I had to come up with a way of explaining the killing) One of these days he might snap again or loose himself completely and end up in the Dark Brotherhood, but that remains to be seen.

As long as you feel comfortable with the way you are explaining things to yourself, go for it!

I'll never understand the need of being "the top of all guilds". My current char' highest rank in his Faction list is Captain of the Imperial Legion, and I'm happy with it. Other than that, I'm Associate of the Fighters/Mages Guild, merely for the beds, a Tourist of the Shivering Isles, and the owner (thus the Lord) of Castle Seaview/Wolfspike. Period. A simple, common Noble who has joined the Legion ranks as a Battlemage, and has gained his current rank (which is nowhere the highest) with blood and fire.

Sometimes you can start a character with some ideas about who they are, where their choices and adventures might take them, but after a while, things might change. I had this idea that my character Eileen would run through the DB questline as an infiltrator of sorts, but now I don't really wish to. She's cemented a reputation as a lawful character, and I no longer wish to bloody her hands. Like Acadian said, you can rationalize quite a lot, but once it comes time to actually put those things into action, they might not feel right anymore. My character just became who she is through hours of play, despite whatever ideas I might have had about who I thought she'd be. These things happen.

I would still like to run through the Thieves Guild and DB questlines again, but I'll need a new character for that. One who is amoral, or worse, fron the very get-go. As for Eileen, Arch-mage and Divine Crusader seem to be up her alley, maybe heading up the Fighters Guild (big maybe), but a life of crime is no longer in the cards. No matter what the rationale may be.