The vulnerability of the first message is a real concern, MTA-STS is not perfect. But it looks like the easiest to deploy tool that can strengthen security for a very large number of messages.
One challenge for your suggestion is that the mail server is often run by a different organization, on a different domain from the receiving address. The HTTPS web server, on the other hand, has a TLS certificate for the mta-sts subdomain of the receiving address. This gives confidence that the MTA-STS policy is set by the receiving domain, not the receiving mail server.
One challenge for your suggestion is that the mail server is often run by a different organization, on a different domain from the receiving address. The HTTPS web server, on the other hand, has a TLS certificate for the mta-sts subdomain of the receiving address. This gives confidence that the MTA-STS policy is set by the receiving domain, not the receiving mail server.