Boston has a great bar scene. Our bars and restaurants are regularly recognized as some of the best in the country. We also have many, many bars for such a small geographic area. IMO the bar scene in Boston is superior to SF.

These are the real pain points for living in Boston as a 20-something:

The T is miserable, always. The weather is miserable, 9 months per year. The attitude is cynical, usually. Massholes are real. Prices are high. We spend too much time comparing ourselves with NYC.

Otherwise, Boston is excellent. The city is clean. People are educated. Some are even attractive. The bike sharing is great.

Bar closing time is not a real issue. It's just a symptom of an old-fashioned, stuck in its ways, puritanical city.