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Fallout: New Vegas Game Add-Ons (DLC) Hints
When should I do this add-on's quests?
1 of 3: The game recommends that you don't start on them until you're at least level 20. That's a good guideline, since this module will take away all of your equipment and regular followers, and will deny you the ability to return to the Mojave Wasteland until you completely finish it.
2 of 3: If you've already build up a character to level 30, your best move will be to get him up to level 35 (the new level cap) by doing more quests and combats in the Mojave Wasteland, and only then go exploring the Dead Money areas. That'll make them easier to handle.
3 of 3: On the other hand, most enemies in the Sierra Madre areas are leveled, and high-level characters will find them to be hard to take down, even if not playing on the highest difficulty setting. As I had occasion to find out, things are especially bad for stealth-based characters who have a low Energy Weapons skill. If you have such a character, and he isn't very high-level yet, you might want to go ahead and do the module right away (if you're ever going to) so that the enemies will be considerably weaker.