What I'd recommend for someone who wants a collection of "cool" cards to share with a kid is to focus less on the condition and more on what makes the card cool.
Usually I say to start with a stack of ungraded commons so you can get an idea of what they should be like, but for some sets that's just not really doable anymore.
Internet purchases can be tougher, even the difference in scanner settings can make something look better or worse. I'm pretty confident in spotting stuff, so if the price was right I'd even buy from a bad cellphone picture. (Like one of my George C Millers... it's pretty beat like the others, but was listed as "old baseball card" with a slightly blurry small picture. ) But to me what makes it cool is that it's one of my favorite sets, and not an easy one to find cards from.
One of my friends asked why I collected cards, and I showed him one card from each decade from 1880's up to the 1990's and explained how the card as a promotional item reflected the country at the time. That might not work for a kid, but showing a card of an old time ball player and telling about him and what he did probably would. My daughters are 7 and 9 now, and I've done that a few times. Not a lot of interest yet, although the older one seems to like stamps, which I also collect. And of course pokemon and magic cards.
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