Itinerary check: Narita_Tokyo_Nikko_Tokyo

G'Day Daniel-san and JR Team

Details: family of five (x5)

Really important is whether to buy a 14 day, starting from Toyko departure for Kyoto?
Or
21 day JR pass starting from Narita_Tokyo_Nikko_Kyoto_Nara_Tokyo_Nagano_Tokyo_Narita (18days)?

Confirmation - is the JR pass good for use to/from Tokyo-Nikko, Kyoto/Nara, Tokyo-Nagano?

Will a JR pass arrive before we depart 15 Jan 2018?

Please check and advise the below summary itinerary:
Day 1 - 18:00pm Arr Narita International,
Day 1 - 19:30 Dept Narita for Tokyo (5ni/6 days) Taito-ku, Nishi-Asakusa
Day 2 - 0900_Japan Tokyo Tower Shibakoen, Minato Goji-ji Buddhist Temple, Tokyo Dome City etc
Day 3 - 0900_Full Day Trip, travel to Nikko, Tochigi Prefecture by Train (3hours), return to Tokyo 18:30pm
Day 4 - Tokyo local sites and visits in Tokyo
Day 5 - 0500am_ぷらっと築地 / 築地場外市場
Tsukiji Fish Market and other Tokyo local sites
Day 6 - 0900 Sat_Shinkansen Train (Bullet Train) Taito-ku, Asakusa Station to Kyoto Station (3 hours 21min)
Day 6 - AM Dept Tokyo - Arr Kyoto (3hours), Shimogyo-ku, Kyoto (01/20-01/24 Jan 18) 5 nights 5 days:
Yasaka Shrine Maruyama Park Shijo Dori Nijō Castle Takotamago - Baby octopus on a stick with an egg in its head.
Arashiyama Bamboo Forest
Day 9 - Full Day Trip_travel to Nara 奈良市, Nara Prefecture return to Kyoto by 18:30pm
Nara Park
Day 10 - AM Wed 24 Shinkansen Train (Bullet Train) Dept Kyoto for Return to Tokyo (3 hours)
OR Option Kyoto to Togakushi via Fukui,Ishikawa, Toyama to Togakushi
Day 10 - Arr Tokyo for transfer/change_Dept Tokyo for (Train JR East Pass?) Nagano (Rtn-Tokyo Day 18) (2 hours 30 min)
Day 10 - Arr Nagano approx 11:00pm; Dept Nagano 12:30-13:00pm by Local Bus? (1 hour) Arr 14:00pm Togakushi
Nagano Prefecture (01/24- 02/01)
Day 16 - Full Day trip travel to Hakubar (2 hours)
Day 18 - Thur 01 Feb 10:30AM Dept Togakushi,
Day 18 - 11am Arr Nagano, Dept Nagano 12:00pm,
Day 18 - 14:30PM Arr Tokyo_Transfer/change for Narita
Day 18 - 15:30PM Dept Tokyo for Narita Int'l Airport
Day 18 - PM Arr Narita Airport
Day 18 - 01 Feb_Dept Narita for Aust.