For Option 2, that description is not accurate.
The JR 吾妻線 [Agatsuma Line] is beyond Shibukawa Station.
Some Local trains
which go on the Joetsu Line from Takasaki Station
continue beyond Shibukawa onto the Agatsuma Line,
heading to Naganoharakusatsuguchi, Manza-Kazawaguchi
or this line's terminus Ōmae Station.
Also,
you can travel by Shinkansen
from Tokyo Station to Takasaki Station.
Probably the simplest option is
: Shinjuku (bus terminal in Busta Shinjuku)
or Tokyo Station (Yaesu South Exit JR Bus Terminal)
-(JR Bus Kanto: Expressway bus)-
Kusatsu Onsen.
This option is relatively slow,
and the bus line is not covered by any JR pass.
The one-way bus fare is around 3000 yen.
http://time.jrbuskanto.co.jp.e.wn.hp.transer.com/bk03010.htmlhttp://www.jrbuskanto.co.jp.e.wn.hp.transer.com/bus_stop/shinjuku_bast...Option 2
: Ueno -(JR Takasaki Line)- Takasaki
-(JR Joetsu Line (until Shibukawa) + JR Agatsuma Line)-
Naganoharakusatsuguchi
-(JR Bus Kanto)- Kusatsu Onsen.
Option 3
: Tokyo or Ueno -(JR Shinkansen)- Takasaki
-(JR Joetsu Line (until Shibukawa) + JR Agatsuma Line)-
Naganoharakusatsuguchi
-(JR Bus Kanto)- Kusatsu Onsen.
Trains | buses for Option 1, 2 or 3 are not very frequently available.
When you make good connections,
Option 1 | Option 3 takes about 3 hours.
Option 2 highly likely takes much more time than Options 1 and 2.
Your additional cost is estimated
at 2200 yen per way for Option 1
and at 700 yen per way for Option 2 | Option 3.
I plan to buy the JR East Pass (Nagano, Niigata Area) One merit of choosing this pass is
that it's a flexible pass which can be used on any 5 days within 14 days.
https://www.jreast.co.jp/e/eastpass_n/index.htmlOn the condition
that you make this Kusatsu Onsen trip within 3 consecutive days,
the JR TOKYO Wide Pass is enough.
https://www.jreast.co.jp/e/tokyowidepass/The both passes cover
the Shinkansen section Tokyo -- Ueno -- Takasaki -- Karuizawa
and the Agatsuma Line.
These two passes do not cover
the JR Bus Kanto lines or the Kusakaru Kotsu bus line.
[Option 1]
Additional cost
: 2200 yen per way for the bus ride.
Tokyo Sta., 06:52,
ASAMA 601,
08:09, Karuizawa Sta.,
08:30, Bus, 09:53.
Tokyo Sta., 07:24,
ASAMA 603,
08:43, Karuizawa Sta.,
09:10, Bus, 10:26.
Tokyo Sta., 08:44,
HAKUTAKA 555,
09:49, Karuizawa Sta.,
10:10, Bus, 11:33.
Note
: The next bus departure is scheduled to be at 11:50.
: The buses depart at Bus Stop No. 2
in front of Karuizawa Station's North Exit.
- Kusakaru Kotsu bus timetables
http://www.kkkg.co.jp/bus/timetable/180421karuizawa_kusatsu.pdf[Option 3]
Additional cost
: 700 yen per way for the bus ride.
Tokyo Sta., 06:08,
TOKI 301,
06:58, Takasaki Sta., 07:26,
Local,
08:49, Naganoharakusatsuguchi Sta.,
08:54, Bus, 09:22.
Tokyo Sta., 07:52,
HAKUTAKA 553,
08:42, Takasaki Sta., 08:53,
Local (for Ōmae),
10:19, Naganoharakusatsuguchi Sta.,
10:26, Bus, 10:54.
Tokyo Sta., 09:28,
TOKI 313,
10:25, Takasaki Sta., 10:44,
Local (for Manza-Kazawaguchi),
12:04, Naganoharakusatsuguchi Sta.,
12:11, Bus, 12:36.