Getting whitelisted and managing your mail server isn't easy and usually costs a lot. I think it's only something that should be optimized when you are sending millions of emails pr. month (like they are).
For everybody else, you can save a lot of time and money by going for Amazon SES, Google App Engine, SendGrid or Postmark (etc.) A lot of these services also include analytics and monitoring and will be cheaper than rolling out your own customized solution (in terms of time and money).
Even for them they would only pay around $6000-$7000 pr. month by using Amazon SES.
Funny how Amazon AWS newsletter gets flagged as spam by gmail each and every time. Even if I tell it 'not spam' each and every month. Something tells me Amazon SES will not get a better gmail treatment.
Has it gotten that bad? I remember back in the mid-90s, when I was still young and crazy enough to fiddle with sendmail.cf on my first few Linux boxen, setting up and running your own mail server wasn't that difficult (and again, I'm talking about sendmail here). Has the whole spamocalypse turned this into an nightmare of that magnitude?
There goes my plan for moving my personal accounts away from GMail before March 1st...
Can't speak for anyone else, but personally I'm getting fed up of legitimate personal e-mails going missing even when sent to long-time friends I've swapped mails with on numerous occasions, only to find they're in the spam tray. These are plain text messages, all sent from the same very small pool of mail servers, with correct headers, consistent From: address that really is me at a personal domain I've held for years, etc.
I should not have to jump through non-standardised and somewhat broken hoops like SPF and DKIM just to get a goddam e-mail delivered to my friend. When you reach that point, it's not your e-mail client or domain registration that's broken, it's the receiving e-mail system that's so paranoid about spam that it's regularly diagnosing and (silently) rejecting false positives.
No - it's not bad at all as long as you have some minimal understanding about what you are doing.
Graylisting + Delayed SMTP prompt + Blacklists + Whitelists works pretty well for filtering incoming spam.
For outgoing mail you just need to make sure that you're not sending mail from a dialup IP range, or some other IP range included in common blacklists. It also helps to register on one of the more common whitelists that are available for free. And of course you need a valid reverse lookup - many mailservers don't accept mails from hosts without them.
I run a mail server on my VPS, did nothing special to set it up, and it mostly works. I probably should look into SPF and reverse DNS and all the other TLAs, since at least craigslist.org silently drops all email from me. There have been two or three other cases over the years. But I'm really lazy and just fall back on gmail for those.
Don't know why you're being downvoted; any business <$1M annual revenue that has to send loads of e-mail shouldn't be wasting time rolling their own solutions
We do more than that, but only send a few hundred emails per day outside of our internal google apps accounts (using sendgrid) and then blast a newsletter once a week via mailchimp.
For everybody else, you can save a lot of time and money by going for Amazon SES, Google App Engine, SendGrid or Postmark (etc.) A lot of these services also include analytics and monitoring and will be cheaper than rolling out your own customized solution (in terms of time and money).
Even for them they would only pay around $6000-$7000 pr. month by using Amazon SES.