The Four New Vegas Playthroughs

First - Energy Specialist
Main tags: energy, speech, repair
Companions: Boone and ED-E
Required perk: Meltdown Perk
Hard at the beginning b/c energy cells weren't very plentiful
Speech made things very easy though didn't side with Brotherhood of Steel and didn't get the Gatling gun
Very fun at the end having found the gauss rifle as it was very powerful
Sided with: Mr. House

Second - Melee Monster
Main tags: melee, unarmed, sneak
Companions: Raul and Rex
Best perk: Raul's companion perk (decreased deterioration of gear)
Easy in most of the game except going melee against Deathclaws with weak weapons
Annoying when trying to close the difference between ranged enemies
Mistake trait: kamikaze (decreases damage threshold and I didn't use VATS too often)
Sided with: Yes Man

Third - The Crazy Build (maxed INT, high Luck and Perception, gimped Strength and Endurance)
Main tags: barter, survival, guns
Essentially a sniper and depends on companions for close range dps
Companions: Boone & ED-E but will replace Boone with Lily for tanking purposes
Taken perks: 3 perks into greater experience gain (30% extra), educated, luck-related perks
Made oodles of easy money gambling thanks to high luck and poker (free money)
Sided with: NCR

Last - The Psycho of the Wasteland
Main tags: explosives, sneak, repair
Required perk: Mr Sandman
Companions: ED-E b/c it doesn't complain about my immoral actions
Boone's body can be found by some shrubs by the dino's feet.. he fell, honest.
Anything that sleeps will not be waking up the next day and everyone else will find a stick of dynamite in their pockets
Loophole: using Mr. Sandman on children, you can't hurt them and you still get xp
Sided with Legion
Journey ended prematurely due to consistent crashing every time the game starts up.