Is it allowed to send newsletter?

Is it allowed to install some script, import emails and send 200 (how much exactly?) per day to my site members?

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Ok, but how much digitialocean allows emails per day? Trying to figure out what is cheaper mailchimp or digitalocean.

As long as you complied with relevant laws it would be allowed. I would recommend doing the actual email sending via a third party like MailChimp which will allow you to manage your list, handle un-subscribes and has a free plan that allows you to send up to 12,000 messages to up to 2,000 list members each month.