As a younger person, and someone who is naturally a bit of a night owl, closing time in Boston is a fairly substantial issue to me. In other places I've lived I typically wouldn't even go to a bar until midnight or so. That doesn't work out too well in Boston. I don't demand that bars shouldn't open until 11PM because that's what time I want to start visiting one, but mandating an early closing time is frustrating to me and generally hinders nightlife in the city.
I obviously don't believe every bar in every neighborhood should be open 24/7, but there's certainly plenty of places in the city that could have a far later closing time and don't even have residential neighbors to potentially annoy. The state-enforced time should be pushed later and decisions beyond that should rest with local government.
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The liquor licensing issues (not enough licenses, exorbitant prices for licenses) in Boston are also something that continues to exacerbate equity problems, and seems to go under appreciated. To my knowledge, Mattapan still does not have a single establishment with a liquor license.
The varied neighborhoods and squares are a big part of Boston, and that many of the poorer sections of the city basically don't have any local nightlife options (and neighborhood/middle class options are hollowing out as well) isn't a problem that should be laughed off/treated as a minor concern in terms of quality of life.
If the license costs $450k and is good anywhere, you have to use it to serve $25 cocktails in Back Bay, not letting neighborhood residents drink a $2 beer and eat some wings while watching the game with their neighbors.