Earbuds for activity. They cancel out distractions and mostly I’m listening to podcasts.
Open-back headphones for gaming and music listening. High dynamic range and side to side balance is important.
Studio monitors for casual listening or movie watching. Best low end response and can move a lot of air.
My car is old enough to have a tape deck. Also old enough that I can fix pretty much anything that goes wrong, and unless I crash it, I fully intend to own it until I die. New cars are for chumps.