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Nice discussion topic
Your comments sound to me more attuned to TRAD leagues than RT leagues but were interesting.
I don't agree with all you said but I do like the idea of trying to always field the best team you can instead of aiming for a terrible record so you can pile up high draft picks.
I agree with you that it is easier to "guess" on position players than pitchers...but disagree with your conclusion. I think you have to pile up a ton of pitching potential and concentrate on that at the expense of position players. Most of that potential won't pay off, but if you get lucky and can get a strong young pitching staff then adding solid position players won't take long and you'll have a strong team for years to come. Doing it the other way you may find you have a good team that just consistently misses the playoffs - a recipe for long term mediocrity. I think a team trying to rebuild (or build) should have a 35 man roster of about 20 pitchers (mainly young starters) as the team tries to find a solid rotation.
Here is a trade question. On a rebuilding team...would you trade Brandon Webb for Lance Berkman? in TRAD...in RT
Thanks for starting the discussion.