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I was planning on using Let's Encrypt until I found out you need to renew every few months. I made a site for a non-profit as a senior design project so I am mostly looking for 1) ability to add billing details then set and forget 2) easy to setup 3) cheap

All certificates need to be renewed and you will always have to do something to renew it. We don't really give recommendations, but your domain name registrar may provide certificates.

You could still use Let's Encrypt on PA by setting up a daily Scheduled Task, which does:

• 1) checks expiration date of existing certificate:

  $ openssl x509 -enddate -noout -in ~/letsencrypt/www.example.com/cert.pem
   notAfter=Apr 28 17:40:22 2018 GMT
  

• 2) compares it with current date and if difference in future is less than a week:

• 3) performs a renew of Letsencrypt cert by executing dehydrated:

      $ cd ~/letsencrypt && ~/dehydrated/dehydrated --cron --domain www.example.com --out . --challenge http-01
  

• 4) sends an email to support@pythonanywhere.com kindly asking to install the new cert from folder: /home/eieiomeisr/letsencrypt/www.example.com/ (for domain: www.example.com);
  also add Cc your address to this message, so you get it once in ~3 months as confirmation/reminder.

Change your username/domain accordingly and maybe forget :)