To me it pretty much comes down to how comfortable you are with the set you are buying. If you are all over the place with your want-list, I would probably just buy graded. But if you collect one or two sets for a few years, you will probably become comfortable enough to buy them raw from reputable dealers.
Sometimes a card will be found by a picker somewhere and if you want it, you have to buy it raw or someone else will and it will get tucked into a collection. I recently found and bought a really tough T207 that was high on my want-list raw and paid $750 for it via ebay. The seller had great pictures that showed the surface so you could see that there were not any surface bends or wrinkles and he had good feedback, so I felt pretty comfortable (and now it is in a SGC 55 holder).
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