I'm sorry, but as a resident of Hyde Park for more than a decade, your experience could not be more alien to me. I have not once wished for the burden and expense of owning a car. Indeed, living here has convinced me that the personal automobile has no place in an urban environment.
Hyde Park is very far from perfect, but its problems are entirely the fault of people with attitudes like yours. You could have bought an apartment close to the shops you'd like to frequent, or bought a bicycle (and now, bike share is a legitimate option). It takes 10-15 minutes to get downtown on Metra, but you probably couldn't be bothered to read a train schedule. And indeed, the problems with Metra—namely, long headways outside of peak hours and lack of fare reciprocity with CTA—would be eminently solvable by a consituency who values freedom from cars. Instead, we have people like you, who will exacerbate our issues by demanding more parking (and hence, necessarily, less density, less walkability, less transit, and less vibrancy). The assumption that everyone will drive engenders opposition to new development, particularly the type of mixed-use development that makes things easy for people on foot.
I'm always dismayed to see this kind of thinking on a site called Hacker News. A true "hacker" would look at the problems of urban living and try to unearth the real causes instead of falling back on the same old kludge everybody uses, buying a car. If you did, you would see that the kludge itself has become the dominant problem.
You feel entitled to easy access to the city, the sort of easy access that is currently offered to drivers and prohibited to anybody else. You're coming from a place of enormous privilege. Living without a car in Hyde Park is, despite your protestations, easy. Living, with or without a car, in most of the rest of the South Side is incredibly difficult. Many people on the South Side are too poor to own a car, or are driven into poverty by needing to own one to access their jobs. By choosing to drive, you are actively making life harder for the majority of South Siders, who would benefit greatly from better transit access and jobs and shops they can safely walk or bike to. Buying a car bought you a bit of convenience, but make no mistake: the system you have bought into immiserates, maims, and kills. We need to think beyond our own immediate comforts and decide to build a city that is safe and accessible for everybody.