So a single trip ticket is definitely more worth it than a 7-days JR rail pass trip right?Yes. Single tickets from Narita to Nagano and back to Tokyo cost around 17,000 yen, which compares to 28,300 yen for a 7-day Japan Rail Pass.
The ski resort should have opened by late Nov right?
Usually yes. But I think it cannot be guaranteed.
Also, how to get to Disney sea from Shiga kogen ski resort?
1) bus from Shiga-Kogen to Nagano
2) shinkansen from Nagano to Tokyo
3) JR Keiyo Line from Tokyo to Maihama (15 minutes)