Let me elaborate. I do a bunch of DC leagues every year, but recently I started jumping into the higher stakes contests. Last year, I had my first Main Event team, and this year I have two teams in the Main Event. While I feel fortunate that I can play in this arena and have an understanding and supportive wife, I do not feel so well off that I think of these as casual purchases. This year, I was lucky enough to get Pick #3 in both of my Main Event drafts (the Thursday and Saturday in NYC). While very pleased with that development, I probably spent an inordinate amount of time in the week leading up to those drafts trying to decide whether, if the opportunity arose, I should take my highest-rated player in both drafts with the 3rd pick or if I should diversify that risk.
For most of the drafting season, my top four players were Trout, Cutch, Goldie and Miggy in that order. Trout was an easy first pick for me and most others (not that I've ever gotten the first pick in an NFBC draft

So, during the days leading up to my two Main Events, as I'm debating internally whether to use my same rankings for Round 1 of both drafts or to purposefully diversify, I also start noticing that Miggy is starting to look pretty good. I catch some of the Tigers' late exhibition games, and Miggy looks like the Miggy I've known and loved (for fantasy purposes) for many years. Perhaps he should be ahead of Goldie, and maybe ahead of Cutch too.
Skip ahead to the Thursday night Main Event. It is starting, and I still am not sure in what order I prefer Cutch, Goldie and Miggy (sounds pathetic, doesn't it?). On the spot, I decide to take Cutch if available. He's been my number two guy all drafting season, and I should be able to grab Goldie or Miggy at number three on Saturday (because after Trout, it seemed like Kershaw, Cutch and Stanton were the most frequent second picks). This will buy me two days to decide whether or not to diversify and, if I do, to decide between Goldie and Miggy. The draft goes Trout and then Stanton, and I grabbed Cutch. So far, so good.
Come Saturday night, I've decided to diversify. I have Cutch on several DC teams and my first Main Event team. If I take him on both of my Main Event teams and he gets hurt, I'm screwed big time. I also decide to pick Miggy. I really like Goldie, but Miggy is looking spry, I go way back with him, and the guy plays 150+ games every year, even when he's been hurt from time to time. Feeling relaxed now that I've made my decision, the draft starts with Trout and then Miggy!

With the exception of my first pick and maybe my second pick, I did not feel compelled to diversify. Although my two Main Event teams are VERY different, I tried to grab as many of "my guys" on both teams, and wound up with four "repeats" and many guys on one team that I would have gladly taken on both had my competitors not gotten in the way.
In any event, after this over-long and rambling post, I am really curious as to how others address this situation. I know many of you have multiple Main Event and/or Primetime teams, or even more expensive teams. If/when you draft from the same spot in these higher-priced leagues, do you stick to your rankings and grab the same guy repeatedly with very high picks or do you diversify (and, if you do, to what extent)? For me, unless it was a no-brainer like Trout, I wasn't really comfortable going with the same guy with my first or even my second round pick. After that, however, I really gave no thought to diversification and just grabbed the best guy available for each particular team. Putting aside folks' personal rankings of the top players, if you had two high-priced teams, would you have taken the same guy with the third pick or diversified like I did? Thanks.
Mike