Agree with your first two points, especially in the comparison to NYC. They're just not comparable from the outset--NY is way bigger (469 sq miles and 8+ million residents, while Boston is 90 sq miles and 600,000 residents).

But I'd say bar closing time is a real issue. I hate having to end my nights at 2, especially if I have to cab it back anyway because the T isn't running.

Actually, that's what I'd say the biggest issue with Boston is--the T service. Not only does it suck when it is running, it doesn't even run when I need it the most. The MBTA is very poorly-managed and many hundreds of millions of dollars in debt (very few actual improvements to the system are done because of this; it will take the MBTA until ~2050 to pay back all its debts under the current structure assuming it incurs no other expenditures)