BOS is my home airport but I really do like it. It's been an on/off focus city for AA and US. Massport has done a decent job with terminal updates lately, especially connectors within B and from B-C-E. Lots of great places to eat (you can do worse in an airport than Legals) and they did a nice job with the AC renovation. AC and PreCheck lines are rarely terribly crowded. Close to downtown and even though I live out in the 'burbs I can get from my house to AC in 30min. The AA experience is a lot better than it used to be there in the mid-00s with often long security lines, the Eagle Siberia gates, and if you're unlucky, an Eagle departure from the Earhart Terminal (worse than the LAX Eagle's nest).

The main demerit is the Massport shuttle buses between terminals and to the rental car and T. It's the only shuttle bus I know that's slower than walking.

For hubs I really do like DCA. If it's ever an option for a connection I'll pick it over PHL, JFK, or CLT. Easy travel to the city. I love the approach up the Potomac, and a little sightseeing tour with every takeoff.

I think ORD gets a mostly undeserved bad reputation. Feels spacious even when crowded, nice ACs, and Tortas Frontera.