1 month Japan Itinerary

I'm planning to go to Japan June 10th-July10th, it's my first time planning a schedule. This is a rough draft of my itinerary, suggestions are much appreciated. I am also wondering if I need a 21-day JR pass or a shorter one with domestic flights. Thanks in advance :D

Osaka 10-18th (7 nights)
Hiroshima 18th-21st (3 nights)
Nagoya 21st-23rd(2 nights)
Yokohama 23rd-25th (2 nights)
(Should I go to Tokyo and Mount Fuji before going to Hokkaido?)
Sapporo & Toya 25th-26th (1 night)
Wakkanai/Rishiri 26th-27th (1 night)
Asahikawa/Furano 27th-29th (2nights)
Abashiri/Shiretoko 29th-2nd (3nights)
Sapporo 2nd-3rd (1 night)
Tokyo/Mount Fuji 3th-10th(6 nights)

Yokohama 23rd-25th (2 nights)
(Should I go to Tokyo and Mount Fuji before going to Hokkaido?)
Sapporo & Toya 25th-26th (1 night)
Wakkanai/Rishiri 26th-27th (1 night)

I think this part is impossible. If you start on 25th from Tokyo, it will take about 5 hours (Flight from HND to CTS and then limited express) to get to Toya. From Toya to Sapporo, it will take 2 hours (by limited express). Further, ou must take bus to Toyako from JR Toya station.

On 26th if you start early from Sapporo, you will arrive Wakkanai at 12:40 (5+ hours train ride) and the ferry take you to Rishiri at 18:20.

Rishiri and Rebun are really nice so I recommend you to go there, but you might consider direct flight from Tokyo to Wakkanai (10800 yen if you take promotional fare for foreign tourists) and then take a ferry. Stay there at least two nights and three or more nights will be better.

How are you going to move?
Tokyo,Osaka,Nagoya,Yokohama,Sapporo is OK by train.

But for example..
You can't go from Wakkanai to Rishiri by train,only by car (Bus is OK).

You had better to get express ticket from Sapporo to Toya.

I reccomend you rent a car especially in Hokkaido.

Thanks for the info guys! The transportation is definitely a thorny problem. Actually, there are 3 of us in total, but we are all college students who don't have a license, so travelling by car is not possible :( made some changes to the draft:
10th-11th(1 night) Osaka
11th-18th(7 nights) Kyoto
18th Nara day trip
18th-20th(2 nights) Hiroshima
20th-23th(3 nights) JAlps(Takayama/Hida/Toyama/Omachi/Azumino/Matsumoto)
23th-24th (Train overnight) Matsumoto - Hakodate
24th-2nd (8 nights) Hokkaido
24th Hakodate
25th Hakodate – Sapporo – Otaru – Sapporo
26th Sapporo - Wakkanai
27th Wakkanai - Rishiri/Reben - Wakkanai
28th Wakkanai -Asahikawa - Furano - Asahikawa
29th Asahikawa - Furano - Asahikawa
29th-30th(Train overnight) Asahikawa-Abashiri
30th Abashiri – Utoro
30th-1st(Train overnight) Utoro - Minami-Chitose
1st Minami-Chitose – Date-Monbetsu – Lake Toya
1st-2nd Lake Toya – Date-Monbetsu – Hakodate – Shin-Aomori – Tokyo
2nd-10th(6 nights) Tokyo/Mount Fuji

I intend to use a 14-day JR pass for my whole trip,but it seems that the schedule in Hokkaido is crazy packed and I am not sure if it will be enough (Assume pass activated on 18th and ends on 1st),should I buy 2 passes instead (like 5-day West Kansai Hiroshima+Hokkaido 7 day?). Will it be possible to somehow visit all these spots or maybe I should just shorten/skip the JAlps and focus on Hokkaido? Thanks again :D

23th-24th (Train overnight) Matsumoto - Hakodate
29th-30th(Train overnight) Asahikawa-Abashiri
30th-1st(Train overnight) Utoro - Minami-Chitose

What do you mean by "Train overnight"?

As far as I know there is no overnight trains in these routes.

You can check your itinerary by using Hyperdia.

30th-1st(Train overnight) Utoro - Minami-Chitose
1st Minami-Chitose – Date-Monbetsu – Lake Toya
1st-2nd Lake Toya – Date-Monbetsu – Hakodate – Shin-Aomori – Tokyo

Theoretically your Japan rail pass is valid if you take the train on day 14 and continue to travel on day 15, but in this route there is no train running throughout the night. Your itinerary seems to be too packed so you might better consider buying 21 day pass and allocating more days in Hokkaido.