Thanks for the thoughtful reply, fabsroman. The Chevy Chase tree protection regulations are quite something. I'm still trying to parse the idea of fines and prison terms that are potentially larger than the maximum penalties allowed by state law. I am not an attorney, but I wouldn't have thought it allowable for a municipality to enforce penalties expressly disallowed by the state.
I've only spent a few days of my life in the DC area, and have no direct knowledge of Chevy Chase's political history or climate. Given how onerous these tree protection measures seem to be, I'm curious how they came to exist. I'm inclined to guess that many of the burdensome granular rules might have been drafted incrementally to address violations of the spirit of earlier, simpler versions of the law... but that's only a guess.
Having lived in some extremely hippy-dippy "liberal" communities, I can say with certainty that liberalism does not correlate very well with nosey, control-freakish legislation. In my experience, liberalism is aligned much more closely with generalized kindness and willingness to live and let live, to keep one's nose out of one's neighbor's business as much as possible -- basically the reverse of the dynamic you're describing. But of course my experience is no more absolute and universal than yours is.
My mental model of these sorts of conflicts cleaves along different lines. I think frictions like these become much more likely wherever lots of people live close together, where the shade from a tree on my side of a property line might fall on your house, and where when you have a conversation on your porch and I can hear what you're saying from inside my living room, even with all the all the doors and windows shut. I think these frictions are exacerbated and the impulse to regulate is increased by the presence of wealth, because wherever people have a lot of their wealth tied up in their homes, they will be especially worried about how one homeowner's actions affect surrounding property values. And I think that the regulations get uglier and more problematic as wealth disparities among people living close together get larger, because the wealthy always have more influence and tend to gain at the expense of others. I think this sort of ugliness works pretty much the same way in "conservative" enclaves like Orange County, CA as it does in "liberal" areas like Chevy Chase.
Anyhow, thanks for taking the time to reply. I think I see where you're coming from.