Just a little add-on for you guys and myself. I'll try to not make every day a chapter by itself, but the start is always the hardest so I believe those early days should also be weighted as such.
Day 1: Chapter 1, 2, 3 (Landed in Konoha, got interrogated, got a stay financed by Anbu and 'met' Iruka and Naruto)
Day 2: Chapter 4, 5, 6, 7, 8 (Used his skills too much, got some money from Hiruzen and had a disastrous conversation with Naruto)
Day 3: Chapter 9, 10 (Playing around with new skills and locating the red-light district)
Day 4: Chapter 11, 12 (Sexy and non-sexy times from early noon 'till night, phew)
Day 5: Chapter 13 (Training for the first time, getting beaten up actually)
Day 6: Chapter 14 (Cole is sore, Hiruzen and Kakashi have another talk)
Day 7- ~14: Chapter 15 (More training)
Day 15- ~16: Chapter 16, 17 (Camping trip)
Day 17: Chapter 18, 19 (Cliff)
Day 18: Chapter 20 (Cole apologizes for being a dum-dum)