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I would like to purchase a VPS and a domain to run my Rails web application on Ubuntu 18.04 LTS. I will send transactional emails using Sendinblue to allow users to activate their account. With regard to server administration, I planned to install services like Fail2ban, OSSEC and rkhunter and configure them to send notifications via email, however I still have to understand how to do it. My first idea was to create an email account at one of the free online services like Yahoo mail, Outlook or Gmail but I was told that, without sending those mails via authenticated SMTP, I would probably be blackholed. I need Fail2ban, OSSEC and rkhunter to send their notifications, so I need to use an email service to only receive and consult those emails, being sure they are not blackholed. What would you suggest? I considered the opportunity to install Sendmail or Postfix and configure them to receive only by the local machine, but at Reddit I was advised to look for alternative solutions.

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I don't know Sendinblue, but in general you'd be blackholed only if you set up your own mail service without necessary certificates. If you use an outer mail account, the things go smoother. If your post sender is able to log into the outer mail service (e.g. Gmail), then you don't need any local mail service. As for the general system mail, take a look at this:

Can I set up system mail to use an external SMTP server?

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