Some great advice
Excellent advice here throughout. With pre-war especially, you'll see a great variance in terms of the eye appeal between cards of the same grade. Some VG's will have Ex+ eye appeal, but will have been knocked down to a lower technical grade due to some flaw which makes the resultant grade accurate, but not necessarily that important to us "connoisseurs," who are looking for value. These cards will be easier to sell and will bring greater $$ in the future than cards of the same technical grade, but which appear ugly for the grade. If the card is not pleasing to you, chances are it will not be pleasing to prospective future buyers either. Leave buying the holder (such as the case of the $100,000 Fleer '86-'87 Jordan rookie) to the so-called "investor." There's so little difference between a so-called "pristine" modern card and a TPG Mint 9 that there is no way you can justify what's being paid for the former, in terms of real value.
With regard to '60's and up (and some would include '50's cards here) cards, there are at least hundreds and in many cases thousands of cards in Near Mint or better, which makes the prospect of any future value increases mediocre at best, unless we see quite an influx of collectors of this material. I would bet that within a given moderate price range, the values will be stagnant or worse, unless the economy takes a dramatic turn for the better. There are a fair number of '20's cards just now emerging as rare and significant, which can still be purchased for relatively moderate prices, which are a far better bet for future appreciation, IMHO. On the other hand, if you're just more a fan of the players of the '60's, and are not all that concerned about any increase in (or retention of) value, buy what you like. The enjoyment you'll get out of your cards will still be enormous!
Happy collecting,
Larry
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