Title says it all.
My biggest booster decision happened last year at a District tournament. I opened my TexP pack and saw Mayhem and Warriors Moses.
My pick: Mayhem
I can't fathom how this could've been a hard choice. Mayhem or Grapes are auto-picks no matter what because of how unbelievably game-changing they are in booster. However, if they weren't in your TexP pack, a Fbtn character would have been the next best thing, outside of maybe Harvest Time or Holy Grail (unlikely as those are).
For the most part in booster, the first round is either the easiest or the hardest, especially with Texp. After that, it's the second round that is most difficult, I think. If you don't luck out with an obvious best pick, things can go down to the wire. I couldn't tell you the number of times I've had to make hard choices.
Do I pick Unholy Writ or Battle Cry?
Do I pick ANB or Hur?
Do I pick DoN or that extra Hero?
Haman's Plot or Emperor Claudius?
Jepthah or Ehud?
Aachan's Sin or DoU?
Blue Bart or Red Peter?
Garrison or Nero?
I think one time many years ago I got a Priests pack with several rares. That was tough.
Some fun things:
Some years back, for two or three state drafts in a row, I got Pentecost in each Priests pack.
I've had a Wrath of Satan passed to me after getting a Garrison in my pack.
I've had a Warriors Moses get passed to me on the second round, while a transfig was passed to me earlier from Ap.
I've seen a draft where someone had a Michael, TSA, and Gabriel, all from Kings. He got some great passes.