Part of the danger of rent-stabilization, as you allude to, is there's no incentive for landlords to improve their units, because the return isn't commensurate to the investment. The apartments decay, the avocado toast appreciates to make up for the stabilized rent, it would seem.
I think that's the issue- it isn't a priority for most, and treated as a temporary nuisance to escape from for many without dedicating much real thought to it. The argument evolves as I work through the piece, but they all flow together I think. The will stems from stigmatization - we have little will to do things we don't believe in (or believe are as important as others). With these two, then comes the housing, which naturally follows. The destigmatization argument at the end was an attempt to tie a bow back on everything to center it back on humanity (what you mark as honesty in your piece, which I like as well), because I was worried it might seem like a market urbanist fantasy with the housing housing housing.
I like how you've positioned rights and responsibilities and the need to allow for some self determination. While I'm murky on the specifics of some of the boundary disputes you mention, I have no doubt SF makes this simple things an order or two more difficult than they need to be. Perhaps it might be as simple as doing away with historic sidewalks, hmm? It's as a good place to start!!