I wasn't in love with Raindrop but that album had just as many killer songs as WTDWYD. The only difference is that it was raw and messy and almost garagebandy, but that's what made the album honest and real. It is hard to listen to sometimes, but it's a great one. However the difference in the first and second album are huge, he really did grow in a short time.
Taking Back Sunday and Midtown tour back in the early 2000s must have been KILLER! I remember they toured with TBS and Underoath at the later part of the career and I went for them and Underoath cause TBS was falling off.
Definitely a too mood-oriented play with this album, though the good songs are GREAT. "Being Your Walls", "Kind of Perfect" and "My Town" are the flagship songs, "Armor For Sleep" and "Slip Like Space" are what really give you a glimpse into the dream-pop sound they would be so well-known for in the future.