Okay so on my third playthrough of the game I plan on being as much evil as I can be and siding with the Legion. I know there are many choices you can make to go down that road and some traits I should acquire but what in your opinion is the proper way to make the ultimate evil on New Vegas?
Interesting cause I recently started the same project. I say this:
Rather than going around killing EVERYONE (too easy), aim for all of the worst endings for each area and faction. Side with the Legion, but see to it that Lanius gets put in charge. As for little factions, do things like, for example.....with Lily,
Spoiler tell her to stop taking her medicine.
and with Boone
Spoiler Make him become a bloodthirsty killer via his personal quest.
or with Cassidy, take her vengeful suggestion rather than a diplomatic one. Simply killing everything and everyone is evil, yeah, but it's so easy. Instead, aim for the worst possible ending for every faction without actually killing them off (unless there is no bad ending for them otherwise). This is rather difficult because a lot of the endings for factions and people require you to be in good standing with the NCR, (Raul, Cassidy and Boone all need to visit NCR-owned areas, Boone needs to do anti-legion quests, there's about two or three game endings that specifically relate to a certain NCR sub-group) so at the beginning of the game you sorta have to support them (sort of, just enough to get all the important quests done) and tick off the Legion in the process, which does mean you gotta fight the Legion assassins at a relatively low level. Then once you've screwed over all the NCR factions, THEN you can finally approach Benny in the Tops. Once you approach Benny, it'll reset your Legion faction reputation adn you can switch over to helping them. After that, getting all the worst endings for factions is pretty simple.