In my experience direct from farmer beef is so superior to store bought beef that I avoid eating beef bought from a store.
I can really only imagining this working out consistently if you really developed those relationships, and for a purchase I'd make a few times a year at most, it didn't seem worth it.
I've found butchers and farmers to be generally upstanding people. I'm also in the heart of farm country. I would be a lot more leery of people targeting a more urban market.
I live alone so a quarter beef would be a real challenge to finish off. Instead, I can go to the local butcher and get the usual cuts, and the unusual cuts, soup bones, hard fat for tallow, and so on.
Where I live, at least, it's all local, beef, lamp, goat, chicken, doesn't matter.
But more generally, steaks just scale well to the high end. They keep getting better and better as cut, livestock, and preparation improves. That's not necessarily true for other foods. E.g., most pastas (while obviously delicious) will only get so good barring a virtuoso chef.
I recommend a test. Find a friend who's really good at preparing steaks. Have them cook a good cut & a regular cut from your 1/4 beef, and you cook one of each too. You'll taste the difference from cut and preparation quality.