I agree about surface and corners. That is much more important to me than centering. However, there are a lot of centering obsessed people in prewar too. My eyes go to the picture and then corners before looking at the borders.
T206s are great investments and you protect yourself from getting altered cards by buying graded. The portrait is the better card, but if you like the dark cap, go with It. It will still be a solid investment.
I would be less concerned about the back than condition. If condition is equal then go for the tougher back. I personally like PSA 6, but nice looking 5 is ok. I feel that is the sweet spot for prewar. When you get to 4, there seems to be a wide variance in condition. Look at cards in PSA's data base and get an idea what cards look like in the grade you want and then try to find one at the top of the range. I am also a fan of buying the nicest condition that you can afford. Although, at PSA 8 and above, I am concerned about altered cards. Collecting in the 80s, you did not see mint t206s. There seems to be a lot more today, just like autographed t206s.
PSA does bring a better a better price, but once you know what the card should look like for the grade, you can see when cards are overgraded and ones that look nice for the grade or even undergraded. I buy both companies because I want the nicest looking card, not the nicest looking registry.
As far as your random questions, those are the things that grading companies look for, so you should be safe buying graded. Both companies have population reports on their websites so you can get a general idea of how many cards are out there.
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