Packing = Winter -Layers, 3-in-1 recommended jacket, water resistant pants, waterproof shoes
Summer – shorts and shirts, rain jacket, comfortable shoes
Transportation = A (overall is pretty good, however suburbs and country side can be expensive and complicated)
Food = A+
People = A+
Cost = B-
Tokyo is awesome! I would say is my favorite Megapolis. Its very high-tech, fast-paced, and efficient but at the same time has a very strong culture where people are respectful, polite and helpful.
Kyoto is very easy to tour. Transportation is efficient and there are maps and signs to get to the pagodas, temples and shrines.
This is right outside of Tokyo, but it can be painful to get to. The high velocity train passes by it, but once you are at the station you can take the regional trains (which are slower) to move from place to place. This can be complicated and time-consuming. Taxis are very expensive. The other alternative to move around is by private tours, which will only take you to the tourist areas.