Yeah, sovereign citizen bs doesn't seem to go very far in the court system. "You have no power over me", seems to be met with "here's exactly how much power we have over you".

Is it plausible that he could have sought and achieved a stay on the fines being accumulated?

There's a city appeals process that presumably he ignored entirely, since his current argument is that city and state laws don't apply to him at all, sovereign citizen style.

Why would he plan to appeal to the US Supreme Court then?

Sovereign citizen beliefs are rarely coherent enough to even ask that kind of question.

Yeah - so the fair thing to do is to make him homeless when he is 80, right? Dude, does it ever occur to you that some rules are wrong and humans making decisions might be wrong? You are responding to the wrong sentiment.

What the city wants is the fair thing, it wants him to clean up his property, its method to do that is to issue citations, and charge penalties for failing to do so. It has said, even today, that it wants to work with him to get a reasonable solution. The headline grabbing fine is the result of a judge saying, your appeal is not valid, therefore you owe the default penalty. $250/day fine for 8 years.

What he wants is to not have the law apply to him, and that's his defense in court, which leads to his "appeal" getting shut down. Which means the ruling just says "you owe the fines". That's how the law works.

The city offers many ways to work through these things before you get fined, and offers many ways to make fines manageable.

But none of that works, if the person is literally refusing to accept that the law applies to him.

I am unsure what you think the correct response is?

The city has said it wants to work with him. The city has been saying that since 2014.

What you seem to be saying is that people should simply be able to say the law does not apply to them, and then simply not follow the law? In response to a a traffic fine, should you simply be allowed to ignore it indefinitely?

If he really can't afford it, that's what bankruptcy (and its exemptions like a personal home) is for, though given how much he's ignored for that eight years it might take a court-appointed attorney to do it for him.

Fines may be attached to the property, not the person, so bankruptcy may not remove the claim.

What’s your point? Do you think justice is being served here? Do you think this is a fair outcome? Do you think this is indicative of a highly functional society?

In a functional society, he would have been prevented from being such a nuisance that he accumulated half a million dollars in fines.

How though?

By enforcing the laws and the penalties proscribed therein.