18 days Itinerary plan

Hi, I will be travelling to Japan for the first time this late march to mid June. In total, I will be travelling for about 18 days.

My itinerary plan is here...hope you guys here can give some comments whether my plan sounds do-able or suicidal:

Day 1: Reach Haneda Airport at 10.30pm. Travel to Asakusa and check into hotel.
Day 2 to Day 4: Sightseeing in Tokyo + Disneyland
Day 5: Morning in Tskuji Market. Activate 14 Day JR pass and travel to Hakone, reach Hakone by mid-late afternoon. Check in at a ryokan. Explore Hakone with two day Hakone pass
Day 6: Check out of ryokan. Continue exploring Hakone. Late afternoon take bullet train to Kyoto. Check into hotel.
Day 7 to Day 10: Sightseeing in Kyoto.
Day 11: Check out of hotel. Take bullet train to Osaka. Spend a full day in Osaka. At night, take bullet train back to Tokyo. Spend a night at Tokyo.
Day 12: Take a very early morning bullet train from Ueno station to reach Hakodate by mid afternoon. Check into hotel. Explore Hakodate the whole day.
Day 13: Check out in the early morning and explore Hakodate morning market. Take bullet train and reach Noboribetsu in the early afternoon. Spend the whole afternoon there. Take a bullet train and reach Sapporo at night. Check into hotel.
Day 14: Sightseeing in Sapporo.
Day 15: Travel to Otaru. Spend a whole day there before going back to Sapporo.
Day 16 to 17: Sightseeing in Biei and Furano. Will rent a car to do the sightseeing process
Day 18: Early morning take bullet train from Sapporo station back to Haneda Airport. Flight departs Japan at 11.55pm.

Along with these...I have a few questions as well:
Qns 1: I will be purchasing 14 JR pass for my trip and will only activate it on Day 5, after I left Tokyo. The pass will last me till the end of my trip (Day 18) right?

Qns 2: According to my flight details, I will be arriving at Haneda Airport at 10.30pm. How likely will I get myself on a train to Asakusa station before the station closes? Taking into account that I do not know the way to the train station and the possibility that my flight arrival might be delayed....

Qns 3: Since I will be travelling around Tokyo, Kyoto and Osaka, which subway pass should I purchase? Pasmo or suica?

Qns 4: I read up about Japan luggage delivery system. Do they deliver luggage from Hakone to Kyoto, and from Hakodate to Sapporo? How do I apply for these services and where do I drop off or pick up my luggage? If its a normal size luggage weighing 15kg, how much will it cost?

Qns 5: On my last day (Day 18), I will be taking an early morning train from Sapporo station to Haneda Airport. Will it be safe to assume that I will be able to reach the airport in time by 10pm to check in for my departing flight?

Sorry for the long post! I do not know anyone who has travel around Japan before, so I can only turn to this place for some advice! Would be very glad to receive any replies! :D

Kat

Looks like a busy but doable schedule.
You should be able to make it to Asakusa but only if you get the 11:34pm monorail or earlier. Otherwise you'll have to get the 12:04 monorail and go to Ueno on the JR line and either walk the 1 or so kilometer to Asakusa or take a taxi from Ueno, or Haneda if you have the money to spare.
You have another option and possibly more time friendly for the trip back and to Sapporo. Get a domestic flight back to Tokyo. Jetstar will get you to Narita for Y4,590 and 6 or so hours less travel time. You can go to Haneda with another airline but you'll pay double or triple unless there is a special or sale.
Sending your bags is a good option but you need to be prepared and generally send your bags 2 or 3 days in advance. It will be about Y2000 and save you a lot of hassle. Have a look here http://www.kuronekoyamato.co.jp/en/ You can generally go to a 7-11 to send your luggage.

You can get a Keikyu railway train right under the terminal at Haneda. Many trains continue into the Asakusa line subway and will take you all the way to Asakusa without changing.

Many thanks for the advice given!

One more question, I was planning on a daily 6,000 YEN budget just for eating and sightseeing purposes (excluding transportation). Would it be a comfortable budget for me to get by?

Kat