Spending money

I forgot to add. Prices in hotels vary during seasons as well as special events such as Golden Week, Festivals, New Year, etc...Spring and Autumn are high seasons because of the Sakura blossoms and Fall colors (mostly end March-beginning April/middle October-end November).
Per my countless search on booking systems, I saw that winter in Japan is cheaper (except Hokkaido and winter resorts). Moreover, two weeks after the Sakura blossoms and before the Golden Week have good affordable prices, and also after the Golden Week from mid-May to June. August is the month of Festivals, and the prices rise up especially at weekends (July is so-so, depends on the days, but it depends on the area, July is cheaper in mainland Japan, while it is expensive in Hokkaido because of the flowers and outdoor activities).

The prices vary between cities too. Tokyo is expensive, well it's the capital, it's obvious. For the Kansai, for example, staying in Osaka is cheaper than staying in Kyoto. Hiroshima also has cheap hotels too. I stayed at Mitsui Garden Hotel Osaka Yodoyabashi, quite cheap to be honest, and it's very modern and clean (also, VERY important, it has a 7eleven right next door!). You only have to walk for a bit to the metro Yodoyabashi stop, but quite easy peasy. As for ryokan, I stayed with a small ryokan run by a family in Kyoto (Fushimi Inari area), it was far cheaper from the high-end ryokans, and the lady gave me such a warm welcome and plenty of Japanese breakfast options.

@rkold - I had guessed you were comparing hotel options in Nagano, but the Metropolitan (part of Jr group) is a 4* offering while a lot of the others are 3* (or 3 and a bit). It has been a long time since I stayed at a Dormy Inn, but they are a good/reliable brand. Occasionally I think about trying one of the others, but my contacts in the area confirm the M is the best offering in town. (And yes, there are many good ryokan in the towns in the region too.)
Your comment on room size is also relevant. Small rooms for yourself is ok, but travelling with someone else, you can be surprised how much time you actually spend in the hotel. I recall talking to some people on a tour with one of the bigger companies and they complained about the terrible hotel and bad rooms - this was a property I use a lot. Reason was simple - they had the worst rooms in the building. I tended to book out the floor with the suites for the same price I would pay for a pretty modest rooms in a larger location.