I have all the DLC for New Vegas and while I love the game I never got around to my "magnum opus" run if you will.
I always enjoyed playing as an evil character who took the entire wasteland for what it was worth, betraying everyone and cannibalizing on their decapitated corpses.
It has been a long time since I played and I know a lot of questlines intersect but I remember I had an elaborate plan that depended on quest timing.
SPOILERS FOLLOW
My entire goal is to take advantage of nearly every faction then kill them, I'm looking to get all the GRA challenges as well as meat of champions.
Also looking to max out skills and SPECIAL if possible.
Also obtaining every possible unique weapon/clothing /armor.

Also (this will be tough I imagine) obtaining all followers.
Looking for advice on quest timing as well as SPECIAL loadouts and the best combination/timing for all perks to make my character an unstoppable killing machine of Frank Horrigan proportions!
I know the timing, quest status and reputation for every involved faction will be very crucial during the events of Kimball's assassination and when ejntering the Lucky 38 and The Tops for the first time.
In my head I don't know if timing will allow but I will be villified by NCR from the start ,by allying with powder gangers do odd side quests for the legion, do a variable amount of quests not involved to either faction, (in no particular order) Dead money when all is wrapped up with veronica, Freeside allied with the kings, brotherhood of steel, establish rep with boomers, white glove etc. enter lucky 38, do odd jobs for NCR, kill the kings confront benny, kill house, attend Kimball's speech and kill him, honest hearts kill joshua graham, destroy the brotherhood, fix Caesars tumor, Old world blues lonesome road ally with Ulysses, bomb both factions kill caesar.
If this makes any sense please reply with any advice you may have!
Many thanks!

Make sure you blow up the securitron bunker under the fort if you're going for evil.