Very good points. I use a third party TLS SMTP server for most outgoing stuff.
Realistically, DKIM, SPF, and other overbearing qualifications should only triggered if you're doing mass mailings. Ideally, you shouldn't get denied delivery if you're using an unqualified personal server (that, as you mentioned, hasn't previously been 100% blocked due to bad behavior by anybody in the past ever).
Realistically, DKIM, SPF, and other overbearing qualifications should only triggered if you're doing mass mailings. Ideally, you shouldn't get denied delivery if you're using an unqualified personal server (that, as you mentioned, hasn't previously been 100% blocked due to bad behavior by anybody in the past ever).