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HankronNaturally, I could write a hundred posts on the subect, but I will distinguish between buying an expensive and inexpensive item. I will and do buy inexpensive items from people I don't know (though check their feedback, determine from their other auctions if they are experienced in the area and know what they are talking about, and am overall conservative in who I buy from), but I would only buy online an ungraded 1933 Goudey Babe Ruth or Ty Cobb autograph from a select few sellers. If I don't know the seller or his reptution, I won't buy such an item from him or her. Simple as that. Do I miss out on some authentic and wonderful items? Sure. I am a very conservative and methodical buyer, but I also never buy fakes or am dissapointed with what I buy.
In all areas of buying, whether in autographs, fine art or baseball memorabilia, I am a firm beleiver that begginers should do their first research on who are reputable dealers. Once a collector has a stable of reputable dealers (which expeands as time goes by, sometimes including that once uknown person who you bought some $7 dollar cards or photos from and were happy with the product), life is easy when you buy an expensive or esoteric item.
I can also promise you that if you are buying from reputable sellers, you will find it easy when it's time to resell the items. When the provenance is included (receipt or printout of the eBay auction), the collector ain't going to have trouble reselling at a premium the rare bat he bought from Dave Knoll, the autographs he bought from Mike Gutierrez or the T206 Cobb he bought from Lew Lipset.