I would think that 100 buyins is more suited towards 9-man since it is pretty regular to drop 10-15 buyins in a day, but losing that same amount of buyins at HU sngs would be an odd occurrence.
And I'd just take a shot at $500s whenever you feel comfortable. I'm sure you are bright enough to realize not to go broke at the above level so you can always move down if things don't go well.
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