As a weeb and history nerd interested in Japanese culture, both Osaka and Tokyo have a lot to offer. However, if you had to choose just one to visit first, Tokyo would be the recommended choice.
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The ideal duration to explore Tokyo is at least 5 days to discover the main areas of the city and the outskirts of the prefecture. To explore Japan's best, spend at least 2 weeks here. Even then, you will realize that there are so many things to discover in Japan.
$5000 is more than enough for one person for at comfortable two-week trip after an economy airfare from the USA and economy to mid-range hotel reservations are arranged in advance.
Kyoto is about 370 kilometers (225 miles) west of Tokyo. It's part of the Kansai region, and thus actually much closer to Osaka: the two cities are about 30 minutes apart on the train. Coming from Tokyo, you'll reach Kyoto before Osaka.
It is considerably cheaper to fly in and out of Tokyo than to include one leg of the trip going through either Osaka airport (flying from US). We would of course save time by flying through different airports since this would help us avoid backtracking, but it is about an extra $350 USD per person.
The best way to travel between Tokyo and Osaka is the shinkansen (bullet train). The fastest type of shinkansen, which is called the Nozomi, takes around 2 hours and 30 minutes and costs Y13,620 for a one-way trip in an unreserved seat.
If you want to focus on one city, Tokyo is the one. However, Osaka offers many similar features and it's a great base to see a whole lot more. Having been to both multiple times, if I were a first-timer again and I can't afford to go to both, I would personally pick Osaka and see everything else around it.
A Little More RelaxedThe Kansai region as a whole has long been characterised as more friendly and outgoing than Tokyo and this is somewhat true. People in Osaka tend to be a bit more open and generally won't hesitate to speak to you even if you're a foreigner.
Osaka 1-Day Itinerary SummaryOne day is enough to get a good taste of Osaka. Stay in a place like Kita, Central Osaka or Minami to save time. The must-see attractions in Osaka are Osaka Castle, the Kita District and the Minami District.
If you're looking for information about a one day trip to Kyoto from Osaka, you're in the right place. Kyoto is a great place to go on a day trip since it's only about 15 - 30 minutes away by train.
Shinkansen or bullet trainIt takes only 14 minutes to run between Kyoto Station and Shin-Osaka Station. If you want to use this option to get from Kyoto to Osaka, you need to buy a one-way ticket that costs 1,420 yen (unreserved seat) or 3,220 yen (reserved seat).
That's certainly a comfortable budget as long as you aren't expecting to eat many fancy meals or do a lot of drinking or clubbing. You can probably save some money with strategic use of transit passes (see summaries on Japan Guide or elsewhere). You should look into the Grutto Pass.
The cost for one person to visit Japan for a week is 155 000 ¥ – 200 000 ¥ (1200 USD – 1500 USD) (bare in mind that it depends on the person/ offers/ period/ and preferences). Food: On average per day a moderate budget tourist spends about 4,500 ¥ on food.