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I strongly suggest not using 3DS for clothes, since then you have to reassign all the bones yourself, one by one - you'd have to be insane to try it. For smaller items like accessories or hairs, it's doable.
Tutorials:3D Meshing Indexwiki - this has a quite detailed explanation of how to use joints and animation, using Milkshape.
Tutorial:Sims 3 Hair Basicswiki - this has a much quicker, less detailed explanation of how to use the Unimesh plugins for working with bones; good if you already understand the principles but need to know how to apply them in Milkshape (use the contents list to jump to the bone assignments section).
You have to do the bone assignments in Milkshape or Blender - other programs lose them during export to the obj format.
Saying that "it gets an error and closes" isn't really useful - what does the error say?
What I lack in decorum, I make up for with an absence of tact.