Yes, the system is weird. Obviously if we were designing a healthcare system from scratch it wouldn't look anything like what we have today. What everyone needs to understand is that the system was never really designed as a cohesive whole but instead evolved over time under what economists call "path dependence". It's not even really a "system" at all in the sense of a unified entity working towards a common goal, but rather a collection of disconnected entities each pursuing their own interests. In particular tying healthcare access to employment seems crazy but it's mainly a result of wage controls that were imposed during WW2. Fixing this is politically difficult because due to economies of scale it actually gives larger corporations a competitive advantage over their smaller rivals.

https://www.ncbi.nlm.nih.gov/books/NBK235989/