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Whatever obstacle is correct and means any obstacle, any at all. Whichever obstacle is also correct but the meaning is different - any of the already mentioned obstacles.
"Whatever" in its traditional sense, such as in "whatever you might think," or "whatever choice you make," is a totally different animal than this kind of teenage use that has spread everywhere and indicates a total dismissal of the line of discussion or the person.
The American Heritage Dictionary seems to allow both: Both whatever and what ever may be used in sentences such as Whatever (or What ever) made her say that? Critics have occasionally objected to the one-word form, but many respected writers have used it. The same is true of the forms whoever, whenever, wherever, and however.
If you go into a public library, you can borrow whatever you want - any book, or any of the videos or CDs if they have them. If you're given a choice of a dozen books, you can borrow whichever you like of that given group. Both words are correct there, but 'whichever' has more of a definite group in mind, whereas 'whatever' is more open.