I've found that Microsoft is the worst of the big players. They heavily rely on reputation of your IP block. I've found the GMail was pretty quick to accept my

I've found that Microsoft is the worst of the big players. They heavily rely on reputation of your IP block. I've found the GMail was pretty quick to accept my domain reputation and I no longer have delivery problems. (Although I don't know what rate you need to send email for them to remember your domain reputation). For personal email a good option here is to use a relay for sending mail (or for sending important mail). Of course the downside is that the relay can see your mail in plaintext.