I've been self-hosting since 2004. I currently route via a VPS. The only issues I have seem to be with outlook.com/hotmail.com/etc - free Microsoft accounts. That goes to junk, though replies seem to work fine. Paid Outlook365 seems fine.

Even after speaking with Microsoft's email admin team on the phone a couple times, I still have issues. It's kind of infuriating.

I have properly configured SPF+DKIM (selector rotated daily)+DMARC, and I've gotten set up with dnswl.org.