For some odd reason, I cannot start this quest on my second character;

What I have done with Boone so far:

-I killed Cptn. Curtis
-Disarmed monorail bomb
-Resqued the power gangers during Booted
-Saved the three NCR troopers hanging at the crosses in Nelson
-Killed Aurelius of Phoenix


I've exhausted every dialogue option I have with Boone and Manny Vargas (the other snipe in Novac)...


What do I have to do so I can do his quest and upgrade his gear?

Did you exhaust every conversation option as you did the quests?

I only ask because I forgot to talk to him after every quest, and it wouldn't start for me either.

I actually had to go back to a slightly earlier save and do those quests again!

Kill Caesar. Drop the radioactive barrels onto Cottonwood Cove.

Game's fairly unstable regarding triggers, reloading and trying those sections again may or may not get it done.

It seems to work sometimes for no reason other than I simply reloaded.

So you have the 5 history points. Just keep talking to him and exhaust the dialogue, and when you ask him if he wants to go to Bitter Springs, he should refuse. Just wait a while and he will stop and tell you he changed his mind, and you'll get the quest.

If you cleared out Cottonwood Cove, which I did without the Radioactive barrels or anything, you have to go back to Searchlight and turn in the mission to Astor, or if you just killed them all without getting the quest, tell him you already killed them and the quest will auto-complete, and the dialogue should be available if you have the necessary history points.