We have been so warned about the difficulties of the first days in Japan
Just curious who "warned" you and what difficulties.
I remember the first time I visited Japan, I didn't have much difficulties getting around, in fact I thought it was much easier getting around than some other places I've been too.
I think a goodguide book and some research before arrival is good basis without the need for hiring a guide to show someone how to get around town, etc.
Now if you are just looking for a tourist guide to places thats a different story, but from my interpretation you're looking for someone to help you get around etc so you can get used to traveling alone at a later point?