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Accepted Answer
I finally ended up solving this issue by following these directions from another thread.
I fixed the problem by putting my root public key to user’s .ssh/authorized_keys file. now I can login from my machine with root username to remote machine with myuser account.
issue this command by root
ssh -p ‘ssh port’ myuser@remoteip
The users home directory needs to be owned by the user in question, as does the .ssh directory and the authorized_keys file.
For example, a slightly different way of doing it that I use.
Create Directories and Files
mkdir -p /home/myuser/.ssh
touch /home/myuser/.ssh/authorized_keys
Add The New User
useradd -d /home/myuser myuser
Add User to sudo Group
usermod -aG sudo myuser
Set Proper Permissions
chown myuser:myuser /home/myuser/.ssh
chown myuser:myuser /home/myuser/.ssh/authorized_keys
chmod 700 /home/myuser/.ssh
chmod 600 /home/myuser/.ssh/authorized_keys
Setup SSH Keys for myuser
echo "ssh-rsa ...." >> /home/myuser/.ssh/authorized_keys
Setup a Password for myuser
passwd myuser
That way you can escalate using sudo .....
Login
ssh myuser@droplet_ip -i myuser
Where myuser is the user we just created and setup, and -i myuser tells SSH to use the key that I have locally on my MacBook.