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DaveWhen I started buying T206 cards, I followed much of the advice here: Start with some commons, not too high a quality, to get the feel of the cards, the buying process, and trimming of these cards, which is all too common. I purchased most of my cards off ebay, a few here.
I started a database of all graded T206 cards sold on ebay, later reduced this to incude only the ones I was missing. I also have kept good records of each card I bought: when, from whom, $, grade - my own if not slabbed. I found that I bought many times from the same sellers. Many of those are here, which I find good deal.
The problem with starting low is that you put the most expensive cards at the end, and if the vintage market continues to climb as it has the past few years, you will end up paying a premium.
Buying cards in slabs is much safer than raw cards, but those cards will carry some premium.
If you really like the SGC holders, they will cross over from PSA or GAI, but no guarantee on the same rating. I've never done this, but I think you can get a new grade first and then decide if you want to break open the old case.
Buying these cards can get really addictive, but is really is a lot of fun and is educational. Just remember that there are over 500 T206 variations (front side only), so the money can really add up. SGC 50 Cobbs usually go for more than $1k.
Best of luck collecting.