[glchen]

I would advise:

(1) Buy raw, but purchase cards with nice eye appeal. (e.g., if your son is focusing on lower grade, then look at cards with slight back damage or other defects that don't detract too much from the eye appeal of the card.) However, for big name cards (like Cobb, Ruth), you should probably buy graded.

(2) If it's too good to be true, it probably is. (e.g., if you are purchasing a card that is raw or not from the Big4 TPG's of PSA/SGC/BVG/GAI, and the HOFer or other big name seems to be really cheap, the card is probably a counterfeit or Altered/Trimmed at best)

(3) Be careful when purchasing raw as if a seller describes the card as VG, it may only be comparable to a card that is graded as poor by a reputable TPG. That is, don't always compare the price of a graded card that is VG to a raw card that is described as VG by a seller. Trust your own eyes and if the seller does not offer a back scan, ask for it.

(4) When possible, compare prices with previously sold history on ebay. This will give you an idea whether you are overpaying for a card, as you should be especially wary of purchasing BIN's as these are typically overpriced.

(5) Always buy cards you like and have fun. If you are always purchasing cards where after you purchase the card, you never look at it again, you should re-assess whether you are really collecting what you want. If you are always unhappy with the condition of the card after you purchase it, you should probably look to collect higher grade cards. If you are constantly selling your cards soon after you purchase them b/c you want to upgrade them, you'll inevitably lose a lot of money which could be going to more cards.

Good luck to you and your son!