[ZWoz]

Putting on my "postmaster at shared hosting company" hat: Used to be. Gmail is done lot of work to be worse than Outlook. At least MS idiosyncraties are somewhat known and stable. I would say that most customer complaints are related to gmail.

[account42]

FWIW that has not been my experience with hosting my own personal mail. The only deliverability issue I had with Gmail was with a newly registered domain and even then they did at least deliver the mails to the spam folder (and soon enough directly to the inbox) which is much more than Microsoft does.

[rstuart4133]

I host my own email too. +1.

[kevincox]

I have a small sample size but for my SaaS which primarily sends email GMail marked as spam for a while but then gained domain trust and it hasn't been a notable issue. Outlook has my IP on a blacklist and doesn't even consider anything else. I need to send via relays to get an IP that is trusted enough for Outlook to even consider my message (which is signed with DKIM + SPF with a DMARC reject policy)