>>2803824
>so many hotels
For tokyo for example, pick an area, akihabara, ikebukoro, asakusa etc. That drastically narrows down the options, then just sort by price, distance to train station, and quality of room (dont get capsule hotel).
>not sure how acceptable street photography
As long as you aren't a dick about it, nor actively try photograph people/faces, nobody cares.
>picrel is random pic i took
>>2803827
Spend time in tokyo. Spend either 1 night or 2 somewhere else like hakone, fujikawaguchiko, then an equal amount of time in osaka as you did tokyo(loads of daytrips).