Is it a Yahoo plus league? I'm thinking it is because your commish is already inserting your keepers ahead of time for the live draft. If it is a Yahoo plus league, then you have to be the last pick. It doesn't start off in the middle of the snake draft process whether it's an odd or even round. If you get put first pick in a Yahoo plus league where players have been put in before the draft, you will have first overall pick of the players that are left. We run our keeper on Yahoo and I always win too
and I always have 12th pick every year.
If it's not a Yahoo plus league, then you will have to moved like you're saying. Your commish doesn't have the ability to insert keepers in a regular Yahoo league. Also, through Yahoo you can edit waiver positions.