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You shouldn't have any problem as tourists. Even if you're with other foreigners that live here, you'll still look like tourists. The only place that's risky is Roppongi, but if you're with locals, you should still be ok, except when leaving bars or clubs in the midnight to 3AM time frame. Also, there have been reports of people dropping roofies and whatnot into drinks in Roppongi (another reason for the Embassy warning), so watch your drink and your coat/purse. Everywhere else in Japan is freakishly safe and friendly. If you forget your change in a vending machine, somebody will probably chase you down to give it to you. If you leave something in a taxi, they'll keep for you. Same with the trains. If you need directions, don't ask a cop, ask anyone, and if they can't explain it, they will probably show you where it is, even if it's out of their way.
The only people that have problems here are the ones that act like total loud tourist assholes or those caught out in Roppongi. If you're with Matt's friends, I'm sure you'll be fine. If there's one word of advice it'd be "Patience". They really are so friendly here, but they have strict protocols and rules for things that they will not deviate from, even if a common sense and expedient solution is obvious. Just be patient and work with it, a solution will present itself.
One thing that is quite different here is restaurants and bars, service-wise. A lot of places have all-you -can-eat and all-you-can-drink (yes, alcohol!) usually with a two-hour time limit. Also, there is no single server assigned to a "section". they don't come around with refills of water or coffee, or to check on how your meal is. If you want something you have to throw your hand in the air and say "Sumi masen!" in a fairly loud voice. You don't even have to make eye contact with anyone (but it helps). This is true even for your initial order. In tourist areas they may be more attentive, but don't be surprised if they aren't. Some places also have a button you need to push that calls someone to your table, even in places like Denny's. They will usually know you're foreigners, and will come fairly quickly, but they may wait a minute until a staffer that speaks some English is available.
One other helpful thing is that you can rent a cell phone at the airport when you get here. I can send a a link with info if you want.
I'm sure Matt knows a lot of this if he was stationed here, and got off base occasionally. If there's anything you have questions about, don't hesitate to send me a PM, I'll tell you what I know.
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The difference between theory and reality is that in theory there is no difference.
"God made man, but he used the monkey to do it." DEVO
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