alleycat is absolutely right! But since I have a lot to share about this topic, I'll still try to answer your questions. (Just my personal knowledge, I might not be right in every single detail!)
I'll be going to Japan in January and stay there until July as a student, learning Japanese at a language school in Toyko. Therefore I already went through all of this!
1. Basically, a work & holiday visa and a student visa are sufficient to work there part time, work visas are quite hard to obtain anyway. Both have a few requirements, for a student visa you obviously have to attend academic institution in Japan, a work & holiday visa has some limits in terms of age, etc. (
http://www.uk.emb-japan.go.jp/en/visa/working-holiday.html) Still, the work & holiday visa is mainly meant for travelling, so there might be a few limitations there!
2. As mentioned above, those two visas in genereal allow part-time working, but there could be a few limitations concerning the job, salry, etc.
3. The Student Visa at least has a few fees which have to be paid to the school, the immigration office and the embassy. (I think around 40.000+ Yen)
4. Absolutely no idea.
5. I will be part of national health insurance, which is completely paid by my school and the governemnt. (This is at least the case for student visa!)
6. Just a start:
http://gogonihon.com/en7. For me it was mainly the experience that motivated me to do this! If you just want to improve on certain skills and work at the same time, I do not know if it might be the wrong choice, but that is a very personal thing!
Hope I could help a little bit