Daily mailing of letters (~300) with an attachment - what?

Question

Mail server

Sending e-mails to your database with an attached PDF file.
The ideal would be software that works through SMTP. Service is an option.
Working, free, moderately fast.

Answer 1

powershell + smtprelay + taskscheduler:
$emails = import-csv c:\temp\emailaddresses.csv
foreach ($email in $emails)
{
send-mailmessage -from $email.from -to $email.to -attachments ...
}
...

Answer 2

I use SPECTral Personal SMTP Server of some old version for something like this (sending out ~100 emails every couple of years). Slow, sad, sometimes with glitches, but it works. I think any smtp server will do.