I’d agree that car ownership makes sense in most cases for exactly the reasons you’ve listed. What I oppose is superfluous, near-daily use that is more for convenience than necessity, and I’m pretty sure such cases are widespread even acknowledging your point about city density. (I’d also add that car commuters from MD and VA are more problematic along these lines than those staying within DC.)

Of course a car makes sense in your case. You do understand that your situation is atypical, though, right?

If he’s willing to accept vulnerability to deployment, I’d consider it. Hell, if he limits his income to the top of the military pay table, I’ll drive his cars down to FL and get them registered for him myself.