Earlier quoted context omitted.
Well, you have no reliable way to assert your personal mail server is not bugged and observed right now. You're one judge's pen-stroke away from having personal property seized and then it's just a matter of how real your machine's physical security measures are.
You have no reason to suspect it either. Yes, in this hypothetical scenario your mail server or your ISP's server might be compromised, and yes, in this scenario, there wouldn't be a big difference. But we don't live in hypothetical scenarios. Paranoia is great and all, but let's be real. An average Joe's personal mail server is more than likely not bugged nor observed, and if communication happens in TLS, then there…
What, precisely, do we "know" Google/Microsoft/FUDCo is doing? Certainly not willingly collaborating with every quasi-legal search and seizure presented to them.