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Exchanging Old USD Notes in Japan: what actually matters to know

Short answer
Avoid airport currency exchanges, as city-based specialized offices offer significantly better rates. Always prioritize newer US dollar banknotes, as older series are frequently rejected or subjected to poor exchange rates at many locations.

From real experience

Exchange rates at Japanese airports are generally unfavorable.
Prefer specialized exchange offices or automated currency exchange machines in urban areas (e.g., Namba Exchange in Osaka, Shimbashi area in Tokyo). Be aware that older 'white' dollar banknotes may incur extra fees (up to 10%) or lower rates at some locations; automated kiosks are often more forgiving.
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In Japan, exchange rates: 1 USD can buy approximately 151-154 JPY in currency exchange offices in cities like Osaka.
Rates of 166 JPY per USD likely represent the selling price of USD. Older USD banknotes (pre-2006) may not be accepted for exchange. Exchange rates can be more favorable in city locations (e.g., Namba) than at airports.
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Exchanging older USD bills (e.g., pre-2013 'blue' notes, like those from 2006) in Japan can be inconsistent.
Some exchange offices, like World Currency Shop in Kyoto, accept them at the standard rate without issues. However, some locations, including automated machines or specific city offices, may refuse them or offer a significantly lower exchange rate. Bills from 1996 are particularly problematic outside of Tokyo, often only accepted at a poor rate or not at all. It is generally recommended to use newer USD bills for better exchange rates and fewer complications.
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The best currency exchange rates in Fukuoka are generally found in the city rather than at the airport.
For example, 'WORLD CURRENCY SHOP' is mentioned as a good option. Specific rates observed in Kyoto were 158.10 at World Currency Shop and 158.20 at Kyoto Money Exchange, while the airport rate was 156.26. Older USD bills (e.g., from 2006) may be accepted at a reduced rate or not at all by some exchange offices; it's advisable to use newer bills if possible.
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Currency exchange at Kansai International Airport (KIX), Osaka: Exchange rates observed were around 151-156 JPY per USD.
The rate of 166 JPY was for selling USD. Older USD banknotes (pre-2006) may not be accepted. While city rates might be slightly better, airport exchanges offer convenience upon arrival. Exchange rates can vary between offices.
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Currency exchange in Japan: Recommended specialized exchange shops offer better rates than banks or airports.
Tokyo: Ninja Exchange, Kawaii Exchange. Osaka: Namba Currency Exchange. These specialized shops are generally more tolerant of older series USD banknotes compared to traditional bank branches.
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Exchanging currency in Japan can be difficult with older US dollar banknotes, as many exchange counters reject them.
For convenience, buying JPY in advance is recommended. If exchanging in Japan, using major USD-to-JPY exchange points or ATMs is standard; rates at airports are typically worse by 2-3 JPY per dollar.
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Currency exchange in Japan: Avoid automatic exchange kiosks due to hidden 8-10% fees.
Opt for dedicated exchange offices in major cities (e.g., Tokyo, Fukuoka). Old bank notes are generally accepted if exchanged at manned windows.
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Inquire about the acceptance and exchange rates for older series US dollar bills in Japan.
Determine if there's a discount applied and how readily they are accepted by banks and exchange services.
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