I'm enjoying the articles - you're taking me back to my rookie fantasy baseball days. I'm up in Canada (where we can't actually find the baseball because of all the snow), so I'm a bit of a late bloomer to the game myself. Over about seven or eight years now, I've learned more than a few lesson. The biggest one though, is to ignore the 'expert' advice out there, or at least take it with a big grain of salt.
My first season, I read a magazine or two and took their word as gospel; now I realize that all they were doing was hyping last years best players. This was the year after Mike Hampton and Jose Lima had career years, for those of you who recall (or admit to!) taking the bait.
One thing that caught my attention in your piece on the draft is your notion of position scarcity. I don't think Hanley Ramirez is a bad #2 pick, or BJ Upton a bad 2nd rounder. They are scarce. Though the field of both 2B's and SS are deep, there are only two or three top tier options. At SS, you've got Reyes, Rollins, and Ramirez (The 3 R's?), and at 2B, there is Utley, then Upton and Philips. After those six are gone, the rest are either "steady" (which is good, but won't win you your league) or unreliable. In the OF, the drop off is not as extreme. Matsui, for example, is a lock for 25 HR, 100 R, 100 RBI, and a decent average. I'd rather have Matsui and Ramirez, than Holliday and an average SS. It's a matter of opinion of course, and really depends on who your later picks are, but drafting your top players based on scarcity is not a bad way to go. Just don't do that for an entire draft.
Looking forward to reading onward in your rookie season. Good luck!