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「I'd just like to know which cities are guaranteed to at least have some English speakers, but be child friendly and not too expensive... I don't need the entire city to speak English, just enough people to where I won't have to worry to much about knowing much Japanese」
For places to live in Japan, there's not really an overlap between places that aren't expensive and places where Enough people speak English that you won't run into any problems if you don't speak Japanese. As others have mentioned, Japanese is the one and only language that the vast majority of the population speaks in Japan, and also the only language for most signs, notices, rent contracts, utility bills, etc.
There are a few parts of Tokyo where English is -slightly- more commonly used (Azabu, Roppongi, Akasaka) because of a slightly larger foreign resident population, but rent and other living costs tend to be very expensive, as many of those foreign residents are in Japan doing government or high-level corporate work.
「I'd like to start a family there too」
The language/expense issue is going to be even bigger here. Generally speaking, Japanese schools don't operate in English, so you'll need Japanese proficiency for enrollment procedures and teacher/parent communication. Schools that are run in English (i.e. international schools) are very expensive.
This isn't to say that you need to be fully fluent in Japanese before arriving. But if you're looking for a place where you can live cheaply and without speaking the language long-term without it being a problem, you're probably not going to find it. That's why most long-term foreign residents of Japan try to linguistically assimilate to the extent they can, rather than relying on the people around them being able to speak English.
「I'm currently dating someone who was born in Japan, but moved to the US around three years after he was born. I decided we should move to Japan, so he can live happily in his home town. But, he gave me the choice of choosing where in Japan we should live. 」
Again, not to rain on your parade, but you might want to have your boyfriend take a more active role in deciding where you'll be living. You mention that you graduated college a year ago, so I'm assuming you're around 23 years old, and that your boyfriend is around the same age. If he moved to the Us when he was 3 that means it's been 20 years since he lived in Japan. That's a long time, during which aspects of life in Japan may have changed from how he remembers them, and he as a person has undoubtedly changed too. In other words, just because he liked living in Japan as a three-year-old to decades ago doesn't mean he's going to like living there now as an adult, or that he'll be equally happy regardless of where in Japan he's living.
「I mostly just posted this for city idea's though, and maybe some other necessary help with all of this.」
Nothing wrong with getting some early feedback. If you're looking for some advice, I'd say:
● Start studying the Japanese language.
Unless you're living on a U.S. military base and never going out into the civilian town, you absolutely will have to use Japanese if you're living in Japan. If you don't speak the language, you'll have a lot more problems and stress, and it's just as important to see if you enjoy speaking the language, since it's something you'll need to do.
Specifically, I'd recommend taking a class or lessons, as opposed to just doing self-study. Self-study is good in a lot of ways, but it gives you an out of skipping things you don't like about the language or find especially difficult, which aren't options when actually using it to communicate.
● Read up on Japan's cities and regions
Asking "Where's a good place to live in Japan?" is a lot like asking "Where's a good place to live in the U.S.?" The answer depends on what kind of lifestyle you want. L.A., Boston, Alaska, and Hawaii are all nice in their own ways, and so are Tokyo, Kyoto, Hokkaido, and Okinawa. But it's entirely possible to love one and hate another, so a necessary step in narrowing down the field is figuring out what kind of things you want to do in Japan.
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