I must say that "weeping and gnashing of teeth" (8.12) is such an interesting image to me. I picture someone off in a dark corner grinding their teeth as hard as they can while they cry uncontrollably - not a pretty picture by any stretch of the imagination, but biblical nonetheless.
Again, there is an Old Testament prophecy fulfilled in Jesus: Isaiah 53.4 (see 8.17)!
Every time I read the Gospels I am reminded about how human the disciples are in their attempts to follow Christ. They doubt, they stumble, they misunderstand, they do exactly what I do in my own life. I will admit that makes me feel a bit better about my staggered path of discipleship!
Oh how often do I need to be reminded that sick people need the doctor (see 9.12)! How often does the church operate as a hotel for the healthy instead of as a hospital for the hurting?
What verse(s) stuck out the most to you in Matthew 8-9?