Travel plans for October...comments?

This is my 2nd trip to Japan...October 2.5 weeks landing in Tokyo.

Day 1 Sunday Arrival - trade in Rail Pass voucher, make train reservations, get to downtown Tokyo hotel (1 night). See anything possible if were are not to tired.
Day 2 - Train to Osaka (3 hrs) in the morning. Spend afternoon in Osaka (aquarium, shopping, food, etc..). I have been here before so I have seen many of the sites. Stay in Osaka for 7 nights (will be my base for the next few days).
Day 3 - Osaka shopping/sites
Day 4 - Kyoto day trip(hit some sites I haven't seen before).
Day 5 - Koyasan trip
Day 6 - Nara and possibly Iga Ueno (ninja town) trip
Day 7 - Kobe/Himeji trip

Day 8 - Undecided day - any suggestions??? Nagoya?

Day 9 - Early morning train to Hiroshima. Day spent at the sites in the city. Stay in Hiroshima for 2 nights.
Day 10 - Miyajima and if time more Hiroshima
Day 11 - Return to Tokyo as early as possible. Afternoon getting settled with some family we are staying with in Roppongi.
Day 12 - Nikko day trip
Day 13 - Kamakura day trip
Day 14 - Yokohama day trip (undecided on this one as well - maybe Matsumoto instead).
Day 15 - Tokyo. Train pass runs out this day.
Day 16 - Tokyo
Day 17 - Flight home at 6pm so morning spent packing and some more sightseeing if possible.

What do you think? I was really trying to get in a day trip on the Takayama Festival, but I am concerned about getting train seat reservations so close to the event.

Any advice or help would be great, but will will be travelling via the bullet train whenever possible so that will help minimize the travel time. We are get and go people that will not spend to much time in the hotel room.

It looks okay. It is quite a packed program. But okay if you like a relatively quick travel pace.

If you visit Koyasan, I recommend to stay there at a temple lodging overnight. It will consume most of day 5 and 6. You could then visit Nara on day 8, the vacant day.

I was really trying to get in a day trip on the Takayama Festival, but I am concerned about getting train seat reservations so close to the event.

Hotel reservations rather than train seat reservations should be your major concern! You could always ride in the non-reserved car (but may have to stand). For hotel reservations, try JTB:
http://www.jtbusa.com/enhome/groupinfo.asp

Boy you dont like to stay still do you :) I couldnt rush about like that I need to have time to stop & watch.
I am also doing my second trip in Oct and our trips will probably overlap. However I take things a lot more gently & allow much more time for deciding on the day. My Itinerary
Day 1: Arrive, check in. Visit Asakusa Kannon temple to celebrate my return. Wander.
Day 2: Akihabara, Shinjuku, light shoppage. Probably the Meiji Shrine to again celebrate my return. Redeem Japan Rail Pass voucher
Day 3: Rail to Hiroshima. Check in stooge about
Days 4-6: Hiroshima, Miyajima, The inland sea
Day 7: Travel to Nara. Nara Park
Day 8: No idea. Possibly more Nara or Osaka
Day 9: Rail to Tokyo via Kyoto to visit a few things I missed last visit
Days 10-12: Who knows. Shopping, temples, museums, day trips
Day 13: fly home

I tried to book a hotel for the Takayama festival this October last April & they were all fully booked. I didnt know about Koyasan. I may have to visit.

Stan:
if you have free days in Tokyo, you could try the Narita area. Narita is actually an interesting little town. Are you familiar with Yanaka, near Ueno? a restfull area, lots of small shrines, art galleries etc. I also like to ride the Arakawa tram line (Otsuka station on Yamanote loop line) towards Waseda university and get off anywhere to see a laid backTokyo few tourist would want to go to.

I will find plenty of things to do in Tokyo :) Narita seems a bit far away, especially as my rail pass will have expired. Thanks for the info, I will visit Yanaka to ride the trams at least. I intend to get away from the normal tourist routes and the Yamanote line is very useful as it is a loop.