It's possible, but first mails to a gmail will often go to spam. I assume that's because I'm on an linode IP at all, vs. something about my server, but I dunno. After contacting people out of band and them un-spamming me it usually goes through, but it is a pain point. Haven't had it with any other destination, I think.

It's possible this would apply to other virtual providers. If it's easy for you to send email, it's easy for spammers...