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Hiroshima to Sapporo by train - best option?

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I'm looking at going from Hiroshima to Sapporo with a JR pass (let's say flying is not an option). I know I have 3 main options:
1) Hiroshima to Osaka + Twilight Express to Sapporo (know I will pay a supplement)
2) Hiroshima to Tokyo + Cassiopeia or Hokutosei to Sapporo (know I will pay a supplement)
3) The whole way on 'regular' trains without sleeper berths

Questions:
- Which is the most scenic route, or does it really make a difference? (I know Twilight express is along the coast?)
- How far in advance do tickets for Twilight Express, Cassiopeia and Hokutosei book up (I would be looking for the cheapest sleeper)? I cannot book until I reach Japan and activate my JR pass (~2 weeks before I want to take the trip - will this be enough time?)
- Re: Twilight express, what days/times does it run? I want to take it in mid-June and likely on a Tuesday- is the schedule out yet? Where can I find it (Hyperdia doesn't seem to have it, and I can't find it on the English JR west site)
- Is trying to get there on a 'regular' train with no sleeper berths a huge hassle (let's say time is not an issue)? Looks like I can depart 7:15am from Hiroshima and make it there by 10:56, with 4 stopovers.

thanks!

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