I haven't ever played Old World Blues or Lonesome Road, but I have them now. I just started a new character not long ago, and he's level 15. I am wondering when I should start Lonesome Road in the story, if it's after you get the chip back, or before, or it doesn't matter, or what. I've also limited myself to level 30 with the trait, so I can't get past level 30 if I should be for the DLC.

Well I would play OWB since it does give some nice build up to Lonesome Road and well can be done anytime doesn't really matter though a fair amount of the dialogue is designed for when you choose to support a faction in the main quest so best time to do it would be a few quests before the battle for hoover dam(so chances are reputation is at its max for the faction you will side with).

Lonesome Road is also designed to throw everything it can at you so level 25-30 is recommended

Level and your progress in the Vanilla main story will not matter. However if you have Dead Money I would play that first with your character (if you haven't already), then OWB, then Lonesome Road. That isn't required at all, but it will leave you in a lot of suspense by the time you start LR and you will probably have a better time. If you do not have Dead Money, do OWB first anyway, then LR. LR isn't too difficult, so you should be fine.

What about Honest Hearts?

I would do honest hearts at around level 10 or so maybe 12. It is a fairly easy dlc to beat for me it was. Old world blues be at least a level 15 id do it at around 18. sierra madre do at level 25 and lonesome road at level 30. I dont take the logans loophole. its better to level up then not get such and such.

Can I do any at level 1?

I left LR till the end. I felt all the other DLC's were building up to it, and a lot of the main game was. I would honestly say it should be the last thing you do before you do the final mission.

How did you know it was leading up to it?

SPOILERS

Well, I won't give too much away. You should know already from at least 2 + hours of gameplay that Ulysses is the Courier that refused the job to deliver the Chip (the one the Courier is shot over, duh) once he saw your (The Courier's, that is) name on the list. Now, he is mentioned in Dead Money by a character, and that same character along with other characters in Old World Blues have interacted with him. Honest Hearts barely mentions him. The point is, by the time you've played all those three DLC, you have some serious curiosity about Ulysses.

If you don't mind spoilers, I could go into more detail about how DM, HH, and OWB lead up to LR.

Definitely. Lonesome Road not only throws the toughest enemies in the game at you, but it's the final piece of the jigsaw regarding the Courier's story. You will need high skills to compete LR and should go in armed to the teeth.

Make it the last thing before the final battle, I'm looking forward to it already.

I made the mistake of playing LR first, in my first play through, not knowing the DLC's are linked through NPC comments. So, now I played HH first, since it's the easiest and you get some nice gear. Then DM (just to get it over with LOL) then OWB (almost done with it now) and then I'm heading into the Divide again. I'm filled with great anticipation to meet Ulysses again! OWB should probably come before DM, but it's really not a big deal, for me at least. For me, DM is great, but also very annoying LOL

I doubt I'd do every DLC for every character, it would take ages to complete the game, and it's nice to freshen things up a little.

My current Van Graff energy weapons character will take on Lonesome Road with some heavy hitting weapons; probably the Sprtl-Wood Gatling laser, and a hard hitting rifle. Honest Hearts can probably be missed this time around, it holds no interest for an energy weapons guy. OWB should be interesting, and has great loot, though I didn't enjoy it as much as the reviews lead me to believe I would.

So the only decision to make is this - do I take on Dead Money for a third time? If I do, it'll be solely for the Holorifle, nothing else. I'm not sure I can do it all again

Lonesome Road is the main event, though. I'm looking forward to that more than resolving the main quest.

I took so much ammo with me it, that in reality I'd have needed a truck to carry it. About 300 missiles, about 500 AM rifle rounds(about half of those were AP), and about 1000 rounds or more for about 5-6 other guns. I was not being caught short on ammo, especially as I was on the first time I played!

LOL yea, well said. I'm only on my 2nd play-through and I wanted to do the DLC's "in order" this time. I'm also pondering if I'll ever to DM again, well maybe later down the road, but not with my next toon. Ugh LOL
I love HH, beautiful area and it's pretty easy, plus you get some nice gear. And I might do OWB again, because of the player housing and some cool perks, as for the Divide, well I am currently looking forward to it and I wonder if the emotional impact will be as great as the first time. Can I handle it a 3rd time? Hmm, we shall see LOL

Lonesome Road is best done at level 25+ or you have the trinity of Marksman Carbine/Assault Carbine, Anti Material Rifle and Riot Shotgun. I would save it for much later in the game although that's only if you want to pick what version of the Courier's Duster you want.

Do it after you have completed all the DLCs and a few quests before the battle for hoover damn.

I would suggest right before the battle of the hoover damn, every thing in LR is about your loyalties to whatever faction you pick. Its also pretty hard, the enemies are some of the toughest in the game

You should do it once you have 100 Sneak and a whole lot of stealth boys, lol. Stealth makes life so much easier in this game.

It's not as fun though, for me at least. Sneak hit that give 1 hit kills gets boring real quickly since there's no challenge.

I done it last and at around level 40+, completed it twice without dying

Play it last.