I run my own mail server. Friends & family, so outbound volume is super low, like 2-3 digits/day, not enough to get a rep. Deliverability was always hard to one of the major providers until I happened to make the right connection on HN to someone who worked there, and she graciously opened an internal ticket, asked some questions about the subnet my server was on, and it's been fine ever since.
Setting aside the fairness of how I got my deliverability problem solved, this now makes me really reluctant to move IPs. :-/
Any tips on IPs where people are seeing excellent deliverability? I'd like to avoid routing my outbound email through one of the email providers (Mailgun, SES, etc) if I can.