I probably won't ever take a taxi again, but have some sympathy for the cab drivers who put their life savings in medallions. The city effectively promised them the exclusive right to give taxi rides, but didn't do anything about a non-medallion entity doing that same thing. They put hundreds of thousands of dollars into something meaningless.
Do you also feel bad for the slumlord who spends a million dollars on a property that eventually gets condemned because he didn't take care of it? Had taxi company owners not used those medallions as an excuse to provide absolutely horrendous customer service, they wouldn't have ever had to worry about uber/lyft/whatever in the first place. I've never taken uber or lyft because it's cheaper, I've taken it because I g…
This is the wrong analogy, for trivially obvious reasons. As I'm sure you're aware, the drop in value of taxi medallions wasn't contingent on the owner being a bad driver. Put plainly, even a driver who went above and beyond to provide honest, high-quality service was affected by the drop in values. To put it yet _another_ way, the fact that many taxi drivers provided shitty service couldn't be less relevant.
Your analogy would only make sense if it was talking about an entire apt block got condemned due to multiple slumlords, including the apt owned by the guy who kept his property up to code and livable.
Neither this nor the fact that the regulatory regime was horribly flawed change the fact that many drivers got screwed through no fault of their own because gov't policy was incompetent enough to create bad policy and fail to sustain it.
Economic ownership of real estate as property is pretty bad economic policy too (cf Georgism) but that wouldn't change the fact that suddenly implementing a 100% LVT would 1) be infinitely better policy and 2) screw over an awful lot of people playing by the rules of the previous system, through no fault of their own.