1. Having left PayByPhone and the parking sector years ago, I don't think I'm one to comment intelligently on current innovators. Quick observation... I still see too much capital being spent on custom, vulnerable, armored, escalating, and gratuitous hardware solutions when simple solutions are already in hand. But that's the classic bias of a naive "software guy" looking at an old-thinking industry, isn't it? :-)
2. re/ parking lots ... Depending on the city, zoning, taxation, and its appetite for redevelopment, a parking lot may be a path for a landowner to pay property taxes and flow a bit of cash while the awaiting the right time to develop it into a new use. The new use may push the same parking, or more, underground. IMO automating parking into something ultradense in urban centres makes sense, but I can understand reluctance to pour capital improvements into land that may change form radically if it's in the path for commercial or residential redevelopment. This is part of the reason we found it easy to sell a low/no-capital solution to parking operators, compared to paystations and hardware solutions. Roaming driverless shared cars that are highly utilized and rarely need to park ... that's an attractive vision, I think. But maybe that starts to look a bit like public transit?
Me, I try to ride my bicycle, walk, and take transit everywhere. :-)