Is getting your mail sent from your own e-mail server past the GMail and Outlook spam filters trivial? I always hear about the aggressive spam filters that thes

Is getting your mail sent from your own e-mail server past the GMail and Outlook spam filters trivial? I always hear about the aggressive spam filters that these providers have which makes it hard to set up your own server. Not saying it's not possible, but I am assuming it is somewhat difficult to set up and their is probably some maintenance that goes along with it. So much so that paying for a provider makes sense. As long as my subscription is the only revenue stream, I see no issue with using a "cloud service" to run email for my custom domain. I'm willing to be the other services have similar situations where you might as well just pay someone to do it for you. $160 to not have to maintain a server room seems like a nice deal to me.