Wow. that was a long post!! ha ha ha!!
The way you determine and draft order is way too complicated.
To answer your qusetion about keepers. I believe that if you keep a player then you forfeit your 1st round pick.
I'm the commish of our league and just to give you another way you might think about setting up your draft.
12 team league, 3 divisions of 4 teams, 16 total players, 4 keepers. a team must keep at least one player to avoid the dreaded dumping at the end of the season.
divisoin winner make the playoff which coralate to week 15 - 17 of the nfl. week 17 being our superbowl.
the next 3 teams make it on record. the last spot or 8th spot goes to the team with the most pts. this way, if you keep losing to teams that happened to score their highst points against you, you are not penalized, but rewarded for scoring a lot of pts.
the last 4 team play for the toilet bowl and the #1. it's round robin. Winner of the toilet bowl picks #1 in rounds 1-10. in round 11 we serpentine. runner up in the toilet bowl picks #2 and so forth.
for playoff teams, if you lose in the 1st round you play a consolation round with the two highest scores who lost play for the better draft position.
the superbowl winner drafts last in rounds 1-10, until it serpentines.
since you must keep at least once player, everyone does not have a true 1st round pick. since the keeper is basically that owners draft pick.
if you only keep one player and everyone else keeps 4 players, then you have the first 3 picks of our draft, siince all other owners will be picking starting in the 5th round.
we annouce our keepers 3 weeks before the draft. once keepers are announced you can not change them.
anyways, sorry for the long post. we've found that this allows teams to know where they are drafting before the draft, teams don't want to dump during the season because they still need to win the toilet bowl, and it keeps all the owners interested til the end.