score:3
First, I really encourage you to read the seat61 page about the JR Pass and train travel in Japan in general
The thumb rule about travel passes is to check manually what the prices are individually for your long-distance trips and see if that would be worth it.
Especially as the JR Pass doesn't cover most of urban/suburban transportation and has exclusions on specific Shinkansen Lines
The reference site in English for this is HyperDia
With the 2 last sectors + the return, you have already broken by far the 7 day 29,650Y JR Pass, and getting the 47,250Y 14 days JR Pass is even worth it
In your case, yes it is worth it.
Though Make sure to be aware of the restrictions linked to the JR Pass, especially around Ozaka
Upvote:3
I'm going to be an opinionated contrarian: you're trying to do way too much in 7 days, and a JR Pass is probably not the most cost effective way to do it.
The rule of thumb is that the Y30,000 JR Pass costs a little more than a full-price Tokyo-Osaka return. But if you're flying into Osaka and out from Tokyo, a Shinkansen between the two will cost around Y16,000 tops (and that's on the Nozomi, not included in the pass) or less if you take a slower service, book discounted fares in advance, etc. Hell, you can even fly for Y5000 or so if you book in advance on a discount carrier like Peach, although getting to/from the airports will add at least a few thousand to that.
Hokkaido is quite large, and it takes a long time to get there from Tokyo by train. It doesn't make sense to spend two days out of your week on trains, and Hokkaido is all about nature anyway, going there and spending all your time in cities like Sapporo, Asahikawa (why!?) and Otaru is a waste.
Instead, I would suggest you explore the Japan Alps between Tokyo and Osaka. Take the train to (say) Takayama or Nagano, rent a car (Y5000/day or so) and drive around, stay in a hot spring, then hop back on the train to Tokyo. This would require much less travel time than going to Hokkaido and still likely cost less than the JR Pass.