[steven]

I don't mean this in a rude way, but how old are you?

To be honest, I think that what you described as your traits will make things difficult here. Do you know how to speak Japanese? Part of speaking/knowing Japanese is being very sensitive to what others are feeling (so an English speaker learning Japanese might take the more straightforwardness of his/her language and apply it to Japanese causing some problems). I think it definitely depends on who you hang out with, but it's best to not be overly sensitive when speaking Japanese as Japanese will say some things that we normally wouldn't say in English which can be taken as offensive.

"I'm bad at knowing when to speak, how much to speak, and when to stop speaking. I just can't pick up on cues like that. "
This seems very dangerous in Japan. Knowing when and when not to speak is extremely important (it's important in English too, but in Japanese there are different reasons, like status, that cause this). Picking up on cues in general is a trait that Japanese people seem to look for. If you can't, you're "KY" or a "hen na gaijin" or "hen na nihonjin".

On the other hand, in general (especially in the work place) there is quite a bit of care taken in planning out schedules and things like that-- straying from which seems to cause discomfort. That's not to say that spotaneous things wont happen here too...

I think that going to another country (especially if you wanna live there) requires a deep understanding, or a deep will to understand the culture. Understanding culture requires quite a bit of empathy. That's not to say that a lot of people don't come here who can't empathize with the culture... I've seen it quite a bit to be quite honest. When you enter a new culture, I think that you have two personas-- your L1 (first language) persona and your L2 (second language persona). I'd argue that a lot of foreigners in Japan have traits more severe than yours as far as their L2 persona goes. These are people who can't really say hello, don't know when to speak, refuse to do even simple things out of a fear that they will embarass themselves or others, cause a ruckus without being able to empathize with the native people, are quick to make quick negative generalizations, and even get angry when things don't meet their expectations. Sometimes they even get angry or impatient when something they are trying to communicate doesn't seem to be working (inspite of their very basic language ablity). Myself included, I think a lot of foreigners in Japan experience some of these things to varying degrees. It's all about understanding your mistakes and learning to move on though. I think it's just a matter of taking more time for certain people. The more time you spend in a culture the quicker you can "tune" your persona "by ear", if you know what I mean (that goes for L1 as well in my opnion).