It absolutely matters to me because I'm not in on my cards for the long haul (meaning, my kids aren't inheriting any of this stuff because they could care less about cards) and I know that when I have to sell them, others will care about the condition and it will matter for me to get top dollar.
As for grading, I rarely pay a premium on a graded card BUT if I find a card worth grading, I'll send it in and sell it at a premium to someone who will.
