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It doesn't matter which order you do them in, as long as Lonesome Road is last as it covers various backstory and plot points.
The order that would be most ideal to do them is is the order of their level requirements, as that's why they're levelled.
The 4 dlc are linked in one big story that complements the main story. Order doesn't matter too much, but lonesome road should always be done last near the end of the game.
My recommendations:
Honest hearts done first, should be done when you first make it to new Vegas before you've met or locked in with factions. The hook of it is that you go on a 3 week trip for 50 caps a day - so makes sense to go off to do it to have ample money to get into Vegas.
For extra back story, stop by camp golf (east of Vegas) and talk to chief Hanlon on the balcony in the main building, he gives lots of back story for the dlc and factions in general.
Honest hearts is also the lowest level dlc, fighting tribals and wild animals.
Next should be dead money. I'd say this one should be done when you're on your way to or from Ceasar camp (even if you don't wanna side with him, it's a good idea to accept his invitation to see what he has to say). Level 15-30 is a good window to do it.
Next old world blues - should be done level 20-40 range and sometime recently after dead money, it has many links to the dead money DLC. I like doing it when I'm doing crimson caravan missions/going to pick up Cass as a companion in the Mojave outpost.
I say this one should be after dead money on a first play through because many of the links from dead money (and if you do it first, you'll like miss many of the carry over stuff/forget about it because certain characters are just random people to you - unless you do dead money first), and the dlc is loaded with damage sponge enemies that just don't stop coming. The experience from dead money will help.
And lonesome road done last, after you have "locked in" with one of the 4 main factions for the main quest, level 35+.
Nice, get ready for a great experience. Follow the intended path, (follow Benny south through Primm and around the long route, do not try to go north from good springs, you will regret that lol) and when you reach the city limits to Vegas is when you should start thinking about DLC, and when the game really opens up.
Also recommend meeting all the 4 factions before you decide who to start with (legion, NCR, Mr house, yes man) and hear what they have to say and their visions for the future. You can side with them all for a bit until you are locked in (when you get the quest "don't tread on the bear" and "beware the wrath of Ceasar" that's the sign that if you continue doing quests for whatever faction triggered this quest, you will be alienated by the NCR or legion respectively. Yes man can always be sided with as a failsafe ending and Mr house has a very clear thing that will alienate you from him if you do it).
Watch your reputations as well, all the factions have reputation scores, and if it gets too low they will send assassins after you. You cannot clear a reputation with a faction once they are hostile, however later in the main story you get one time that the NCR and legion will reset your bad reputation with them, and one time only. After that if you make them enemies again, they will be after you forever.
You can have up to 2 companions with you at once, one humanoid companion and one non humanoid companion (there's only two of these). There's 8 in the main game.
Your first companion can be achieved in Primm (non humanoid companion) though you need recent science or repair skills, or must salvage some junk which it will specify.
The next companion is at the Mojave outpost, but cannot be recruited til later after you get to Vegas.
After that novac is where the next companion is located.
Black mountain is another, and jacobstown has another. One in the 188 trading post north of novac. There's also two in freeside outside of Vegas (one non humanoid).
All companions have a side quest associated with them, and one companion's side quest even changes the final battle a bit. So it's best to recruit them all and get them to wait at your home (you will get a player house you can send them to once you reach Vegas proper) and swap them out on various adventures.
All companions also have different abilities when you recruit them. One companion for example makes it so all enemies glow red when you aim down your sights, another makes items lying around glow green when you aim, one doubles the distance of the enemies that show up on the radar, one makes consumables heal more, one slows decay of your gear, one removes negative effects from alcohol, one is a walking work bench, one doubles the length of stealth boys.
They all use different weapons and have different skills, some are better with energy weapons, some melee, some guns, etc .
Three of the dlc have companions. Dead money is centered around companions as part of the story, there's three of them. Honest hearts has two companions and a side quest for each. Lonesome road has one non humanoid companion which is essentially the same companion you can get in Primm, and his upgrades from the dlc will carry over to the main game.
Unfortunately none can leave the dlc area.
Old world blues locks you in until it's main quest is completed (but it has a lot of side quests) and afterwards you can return whenever as it becomes a super player home (which you can teleport to).
Dead money locks you in until it's complete, and it takes all your stuff (you get it all back when the dlc is over) and you cannot ever go back after you leave (so do everything and explore before you finish the quests here).
And lonesome road you can enter and leave whenever you want.
No companions can follow you to or from the dlc locations.
Btw, just so you know, New Vegas is one of those games that's best played through multiple times. I've had quite a few playthroughs, and I discover something new almost every time.
Happy trails!
Unlike in Mojave Desert, DLC enemies DO scale in terms of skills and gear. I once tried HH with 40+ lvl character and noped out of it when I saw first White Legs packing a brush gun.