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Fallout 3 Game Add-Ons (DLC) Hints
New Equipment Tips
What stuff you get each time doesn't depend on what order you do the six side areas in. Whichever one you do first, you'll always get the items in the "First-Time Equipment" list. The same goes for the second list, and so on. You don't have to pick everything up as soon as it's available -- you could wait until you've done all six side areas and then start collecting items.
NOTE: If you don't find the equipment you should after going through a side area, it may be because you didn't clear it of all hostiles. Go back and do so, then return and see if your stuff has appeared.