One is the polished premium default. The other is the maximum-centrality business-core answer.
Travel angle
For most leisure trips and first visits, Back Bay wins because it feels better while still staying highly central.
Move angle
For everyday living, Back Bay is easier to defend unless your routine genuinely depends on downtown access and you care more about centrality than neighborhood mood.
One is the practical core-edge answer. The other is the charm-first premium classic.
Travel angle
For romance and classic leisure stays, Beacon Hill wins. For hospital, event, or utility-driven stays, West End is usually the cleaner answer.
Move angle
For most charm-first buyers, Beacon Hill is more emotionally distinctive. For people who need newer-building function near the core, West End can be easier to live with.
More range and relative value on one side, more social gravity and higher-demand identity on the other.
Travel angle
South Boston is the more plausible stay pick because it is easier to use as a social neighborhood base. Dorchester only makes sense for a stay when you have a specific local reason.
Move angle
Dorchester usually wins for value-aware long-term decision-making. South Boston wins when neighborhood feel, social gravity, and core-adjacent identity matter more than stretching the same budget.