An addiction can work well in some environment but completely destroy you if your environment changes.
Also, I'm not convinced that caffeine addiction is completely overcome in the week or so it takes for the physical withdrawal. Even for myself when I decide to go through long periods of decaffeination, I find that my energy and motivation is significantly deteriorated from when I regularly caffeinate. Sometimes I wonder if my regular use as a college student permanently altered my brain chemistry. On the flip side, maybe this use set me up for the early career success that I might not otherwise have achieved.
Again, the problem is availability, and we've decided in this country (and most countries) that caffeine should be widely available. So it's not a significant problem, and is easy if slightly time-consuming if you need to update your context.
It's probably worth tying this discussion into applications to e.g. the war on drugs, but the language there tends to be so hyped up that it's too hard to have a good discussion about it.
Which makes you wonder how much drug use would be merely 'dependence' if we had free and easy access. I suspect it is a drug-by-drug case, depending on length of trip, relative incapacitation, physical dependencies (/withdrawal), rate of tolerance increase, etc.
The only downside is that I have to be slightly prepared if I am not going to be able to easily consume my regular doses of caffeine. And if I want to cut/stop, it takes about a week or so to do so comfortably.
As for the glorification, I think it's really a glorification of workaholics, and 'needing coffee to get through yet another pile of TPS Reports' is more a badge of honor than anything else.