Big stations often have English-speaking staff who can help with picking the best train.
Most offer horseback riding and at least some English-speaking staff.
Just east is the Ueno motorcycle district, with English-speaking staff available in some stores.
Some rental agencies that usually have English-speaking staff on hand:
If you can't find what you want, the English-speaking staff will order it in.
Also notable is the pharmacy with English-speaking staff and the small bookshop upstairs.
But in local establishments, one is very unlikely to find English-speaking staffs.
The mostly English-speaking staff at the visitor centre are very friendly and helpful.
Since this place caters to the expat community, the English-speaking staff is used to dealing with people like you.
The helpful, English-speaking staff will tell you when the next train is due.