JR Wide from Ueno to Tobu World Square

If I using the JR Wide Pass, is my entire trip from Ueno Station to Tobu World Square fully covered? If not how can I maximize the usage of my JR Wide pass to there?

The pass you mention is this one? (https://www.jreast.co.jp/multi/en/pass/tokyowidepass.html)
If so, it'll cover all by using the following route:

1. Take Tohoku Shinkansen from Ueno to Utsunomiya.

2. Take a local train from Utsunomiya to JR Imaichi station.

3. Walk from JR Imaichi station to Tobu Railways' Shimo-Imaichi station. (It'll take around 15 minutes according to Google maps)

4. Take another train of Tobu Railways from Shimo-Imaichi to Tobu World Square station.

Please not that this is not based on my own experience, but it looks okay.

JR Tokyo wide pass=10180 yen
But you can go from kita senju st to Tobu wor ld square by paying 1400 yen by Tobu railway

JR Ueno Station is huge and complicated.
I recommend you in advance check how to get to the platform.
(Where will you stay for the previous night?)

When you purchase your JR TOKYO Wide Pass,
reserve your seat in the JR - Tobu through Limited Express train.

Route fully covered by JR TOKYO Wide Pass:
Ueno Station
: Track 2
(around 09:00)
| JR Yamanote Line ((counterclockwise))
(around 09:20)
Track 6:
Ikebukuro Station
: Track 3
(09:40)
| {Limited Express SPACIA Nikko 1}
(11:22)
Shimo-imaichi Station
(11:43)
| Tobu Kinugawa Line {Local}
(12:05)
Tobu World Square Station.

You also can change trains at Omiya (using Tohoku Shinkansen or any other JR lines from Ueno), or at Ikebukuro (using JR Yamanote Line from Ueno), and get Tobu Railways' special express train at each station to Tobu World Square. Those routes require you a transit only once and are much easier, but there are only one or two train which go to your destination, per day. If your special express train stops does not go to Tobu World Square directly, you'll need trans once more at Shimo-Imaichi Station.
So please check the timetable carefully.

you'll need change trains* once more