Alternatives to using passwordless sudo [migrated]

• Given that I’m the only human who should have access to a Linux server, what are the major security risks associated with updating sudo to not require a password for my local user?
• Are there other ways of making sudo less cumbersome without running everything as root?
  • I’ve already increased the timeout so I don’t have to enter my password very often per session, but for other reasons I end up disconnecting several times per day.

I have a Linux server (hosted on DigitalOcean) running a fairly popular website.

My normal process is:

• SSH into the server as michael (uses my SSH key with I’ve already added to my ssh-agent)
• When I need to run something as root (to restart a service, edit cron jobs for www-data, etc):
  • I use sudo [cmd], which requires michael‘s password
  • I copy that password (a long random string) from my password manager and paste it into the terminal

One of my colleagues says they don’t bother with a regular user account — they always SSH as root. I’d rather NOT do that — I like knowing that I won’t accidentally cause serious problems unless I use sudo.

It would be nice, since I’m the only human who logs into this server, to SSH as a regular user but still not have to enter a password to run something as the superuser — without substantially increasing risk.