SO I just tested. After working out that on macOS I now need to use nc -c instead of telnet... I _can_ send mail manually, but it _does_ end up in gmails's spam folder saying "Why is this message in spam? It is similar to messages that were identified as spam in the past."
Iain-2:~ iain$ nc -c gmail-smtp-in.l.google.com 25
220 mx.google.com ESMTP k5si5682618pls.209 - gsmtp
EHLO elided.org
250-mx.google.com at your service, [202.171.181.100]
250-SIZE 157286400
250-8BITMIME
250-STARTTLS
250-ENHANCEDSTATUSCODES
250-PIPELINING
250-CHUNKING
250 SMTPUTF8
MAIL FROM: <bigiain@elided.org>
250 2.1.0 OK k5si5682618pls.209 - gsmtp
RCPT TO: <bigiain@gmail.com>
250 2.1.5 OK k5si5682618pls.209 - gsmtp
DATA
354 Go ahead k5si5682618pls.209 - gsmtp
Subject: Test
From: bigiain@elided.org
To: bigiain@gmail.com
Date: Fri, 31 Jan 2020 13:07:00 +1100
Foo baz nah
.
250 2.0.0 OK 1580436443 k5si5682618pls.209 - gsmtp
QUIT
221 2.0.0 closing connection k5si5682618pls.209 - gsmtp
Iain-2:~ iain$