I have far less experience than everyone else in the league, so I'm not sure how helpful it is to read about my thought process, but here goes:
Looking at recent DEAL drafts as a model, I decided I wanted to pick close to the back of the draft. Pick 24 would me 6 picks in the top 75. Pick 20, which I got, gave me 6 picks in the top 87. My sense was that you could guarantee six excellent players, even if you had to forego the very best guys early in the first round.
Pick 1.20
C
Ty Cobb
I decided that I would just pick the best player available here, without concern for letter. When a few people I didn't expect flew off the draft board I got hopeful that King Kelly or Hugh Duffy would fall to me. They both went right before me, so I grabbed Ty Cobb. I never really regretted the plan to ignore letters early, but it did certainly take a lot of Cs off the board.
Pick 2.05
S
George Sisler, Tris Speaker
As I made my first round pick, I was already thinking about who might be available in round two. My dream would've been Ted Williams and Honus Wagner or Mantle and Morgan so that I could get a stud hitter and fill a middle infield position, but they were gone. I toyed with some great pitching Ks (Kershaw and Koufax, or maybe even Keefe?) or a Joe Jackson and Hughie Jennings combo. But ultimately I couldn't pass up two terrific hitters in Sisler and Speaker. I've now used two good letters and only have two OF and a 1B, so I like my players, but haven't been paying attention to needs like position or letter scarcity.
Pick 3.05
G
Eric Gagne, Ron Guidry, Tony Gwynn
I was surprised that Keefe and Kershaw hung around for so long and there were some Bs who went just before my pick (Brett plus either Bieber or Bender). I got really excited about Garciapara, Gehringer, and Gagne, but the middle infielders went off the board before I picked in the 3rd. I stuck with Gs, adding a decent SP and, hopefully, my DH. I considered McGraw, Mays, and Ed Morris, but I decided I didn't want a huge inning guy -- I've just never figured out how to effectively manage them.
Pick 4.20
R
Tim Raines, Toad Ramsey, Jose Reyes, Fernando Rodney
This was an insanely long wait, with great players flying off the board (137 picks). I knew I needed to address some needs (middle infield and pitching) in this round and the next. There was no one I got here that I was super jazzed about, but this finished up my OF, got me a decent SS and helped my bullpen.
Pick 5.05
M
Buddy Myer, Kenta Maeda, Dave McNally, Juan Marichal, Cla Meredith
I had to decide here whether to sure up my bullpen or my starting staff. I knew I'd have another long wait coming, so whichever I ignored would be a possible pain point. With Gagne and Rodney already in my pen, I decided to go with starters. Two picks after me 3dayrotation grabbed up the B relievers I would've targeted (Betances, Betancourt, Britton). The starters I got locked me into a low WHIP, high HR strategy.
Pick 6.20
L
Freddy Lindstrom, Seth Lugo, Paul LoDuca, Hans Lobert
At this point I needed 2 catchers, a 3B, tons of RPs, and backups. I thought Lindstrom was easily the best available 3B, given my team makeup, so I build this round around him. LoDuca gives me good defense behind the plate. Lugo isn't so great, but is useable. And Lobert allowed me to lock in Palace of the Fans.
Pick 7.05
U
Koji Uehara, Chase Utley, Jim Umbricht
Uehara was the best RP around, especially given my pitching staff setup and home stadium. Utley would be a nice backup at 2B and 1B. But there was really no one else available with the letter U. That said, I knew Uehara would not make it back to me at the back end of round 8. I don't typically use mop up guys, but decided to take a chance that I could make this work with basically two dead spots in the lineup (Umbricht and Lobert). I'm not sure that was the right strategy.
Pick 08.20
F
Keith Foulke, David Fletcher
End game here. I need a catcher, an RP and a backup SS (who ideally can also play elsewhere). I knew I wanted Bassler as my catcher, but there were other guys I could've grabbed if he got taken, so I went with the multi-eligible Fletcher and the lots-of-innings Foulke.
Pick 09.05
B
Johnny Bassler
I was glad to get a lefthanded hitting catcher with a decent arm with my last pick.
Final roster
C: Bassler/LoDuca
1B: Sisler
2B: Myer/Utley
SS: Reyes/Fletcher
3B: Lindstrom/Lobert
OF: Cobb, Speaker, Raines
DH: Gwynn
SP: Guidry, Maeda, McNally, Marichal, Ramsey
RP: Gagne, Rodney, Uehara, Lugo, Meredith, Foulke, Umbricht
My main concern is that playing in Palace of the Fans, and with effectively only 23 players, I won't have enough innings (1622 without Umbricht). We'll see. Anyway, this was a very fun draft -- I'm eager to see how the season goes.