Answers that I am looking for:
step by step description with images or fixing on the server side.

I have read thru a couple of questions/guides, but non of them has answered my question.
I highly recommend to just use AWS if you are at this point it is simple to set up if you follow a guide step by step and than it actually works unlike Digital Ocean.

I am trying to set up a droplet server and it fails at the beginning.
macOS 10.12.6, normal terminal.

I am following the guide of https://www.udemy.com/course/the-ultimate-beginners-guide-to-django-django-2-python-web-dev-website/learn/lecture/9517142#questions

the guide and I use e-mail password
For him it just step by step gives the correct:
I can SSH my IP Address EX (the 100s just example).:
ssh root@100.100.100.100

I can copy and paste and pass the next password question with the email. And that works fine

but I cant step thru the following part
Changing password for root.
(current) UNIX password:

I always type in the same thing and than it(the 100s just example):
Connection to 100.100.100.100 closed.
than I start the whole thing again and it never asks for anything different

for the guide guy in the 2nd cycle it asks the following, but for me not:
And I never get these parts
Enter new UNIX password:
Retype new UNIX password:

Thank you for the help.