Dennis Gorelik

No, in most cases such problems can be sorted out, but if recipient's mail server is private, it tends to be simplier (if problem even exists). Google Mail have not only the tendency to mark clean mails as spam and move them to the junk folder, but even discards some mails without any trace at all, - this "feature" is insanely annoying. Russian free mail providers are even worse, e.g. one of managers in one client company likes mail.ru web interface and hates Outlook/Thunderbird alternatives (mail.ru portal can work as a mail frontend to a corporate mail server if you enter email and password) and nearly all unexpected mail behavior in that company, when I compelled to dance around, goes from crazy and constantly changing internal mail.ru message processing logic. Anyway - Google doesn't dance around problems, it creates them at enormous rate because of constant code and logic refactoring. Google works more or less stable only with Google.

No, one hour of creating a VM and configuring Postfix/Dovecot/Spamassasin/Sieve/Roundcube for next 5-10 problem-free years of uptime without any admin activity except free space monitoring - it's not time consuming at all. :) There is a simple rule: if you can live in the hotel for many years - you can safely use GMail or Cloud Exchange, but if you want to be able to hammer some nails into the wall or change the furniture - you need your own home. The range of opportunities in that cases is simply incomparable.