I'm at the point of the game where I just got "Don't Tread on the Bear". I'm currently in Gommorah doing "How Little We Know", and "The House Always Wins" quest in Gomorrah. I;m not going to turn the latter in however, in fear of alienating the NCR(Haven't decided who I'm going with yet). I have not done any of the the Extra content as of yet. When should I start?

It's the right time to do it. What level are you? Some DLC's will warn you about level requirements and it's advisable to obey them.

Start Honest Hearts after you kill Caesar (if you are gonna kill him) trust me, the trouble is worth it all.

Is there a specific quest I need to take to kill Caesar or do I just run into his base, kill him, and then flee?
Also, I'm level 15, soon to be 16.

Kill that [censored], i suggest killing every Legion dog with him, as it is very hard to just run into the base and flee, if not impossible. Take alot of weapons and ammo. Dont know if there is a quest for it, i have always just taken him and all he′s soldiers out in one run.

I'm going to need ammo. Lot's of Ammo.

Well normally I do it terms of

Honest Hearts-Before Entering the Strip
Dead Money- After choosing an alligence(Mostly around geting the Boomers for help)
Old World Blues- Around the mid way point of each factions questline
Lonesome Road- Near the final battle


I wouldent recormmend killing caeser till after Honest Hearts since it does connect him alittle in backstory, though I wouldent recormmend killing him anyway

[censored] that up. Any particular reason as to why?

Honest Hearts is the least linked to the DLC story and from a roleplay prospective my characters wouldn’t just join on a expedition to Zion for a few weeks when deciding what faction to join and the DLCs incentive of earning some caps, given that the factions are promising something much more then caps makes it abit obsolete (unless perhaps my guy was apart of the legion)

Will it really screw everything up if I did Honest Hearts now? Technically, I haven;t even decided whom I;m siding with...

No not really, just from my view its best to start before the strip but can really start the DLCs when ever, though I would always recormmend doing Dead Money, Old World Blues and Lonesome Road in that order since they refrence each other quite heavily and builds up the background plot to them

I found Honest Hearts the easiest, as it scales to your level and is fairly linear. I would definently do that one first. After that,I'm not sure. Personally, I found both DM and LR very hard, but that's just a personal opinion.

No, many people rp that the reason they are going on a expedition up north to zion is because they need caps.
You can just find some reason that fits your character and how deep u are in the main quest, if u want. It isnt game breaking so dont worry.

Depends, but I usually do Honest Hearts before I enter the Strip for the first time on the notion that I'm joining the caravan north as a means to make the caps necessary get into the Strip.

Then I return and do Old World Blues after I've hit level 20 or so and have advanced to about the halfway point in the main quest line.

Then I do Dead Money when I'm done with Veronica's quest (if I do her quest in that play-through) or when I get fairly close to the end of the main quest line.

I save Lonesome Road for when I have only the second battle of Hoover Dam to look forward to when I return, and that means that all of my business in the Mojave is concluded -- including any side quests that I wanted to complete.

I would do dead money and then OWB, cause u do get alot of info about big mountain in dead money which makes u kinda wonder waht really is there, so it would fit more to do HH-DM-OWB-LR in that order.

I find that you can do the DLCs at any time. They provide some specialist equipment so the earlier the better but you do need to be fairly high level to do well in them. Whatever you do you will need some carry space, they give you lots of cool stuff

Lonesome road should be saved for last.

I usually do Honest Hearts around level 15, Old World Blues around 25 and Lonesome Road I wait until I'm halfway through House's Faction quests. Dead Money I avoid like the Plague, for someone else probably around 20-25.