Which Itinerary for Senior Traveller?

Hi, My Family of 5 (3 female adults and 2 Senior (55yrs plus)) will be travlleing to Japan from 15 May to 25 May 09. Arriving in Tokyo.

I am in the midst of planning the itinerary.My concern is my elderly mother who has some difficulties in walking. She can't really walk for a long period and tired out easily. However Japan has been a country that she wanted to visit a lot. Also because of her difficulty, she does no like to join a tour group, which is inflexible in their travel plans.

My dilemma is in the planning of the itinerary.
I am deciding on either to bring her to Hokkaido where self-drive will be possible and since May is also a good time to visit or traveling to a few places in Japan (Tokyo, Hakone, Osaka, Kyoto and Hiroshima) to give her a full flavour of Japan.Likely that it will be her last trip to Japan.

Luggage Carrying is also an issue. Not sure if it is possible to enjoy the trip with the luggages and travelling between places.Is the takyubbubin services easy and good to use?

Do we have to pay for the parking at hotel in Hokkaido if we are guests staying th ere? What are the general charges for tourist attractions?

Thank for the advice if any.

I recommend to pick the places based on your interests. For transportation between Hokkaido and Honshu, I recommend the plane. Renting a car in Hokkaido sounds like a good idea. In the other cities, I recommend to use taxis to reduce walking distances.

Delivery services are a very efficient way to send your luggage from airport to hotel to hotel to airport, but delivery usually takes at least one night:
http://www.japan-guide.com/e/e2278.html

Do we have to pay for the parking at hotel in Hokkaido if we are guests staying there?

In big cities, generally yes. In small towns and on the countryside, generally no.

What are the general charges for tourist attractions?

0 to 2000 yen per person:
http://www.japan-guide.com/e/e623a.html