Ask Paul: June 13 (Premium)

Every day feels like Friday the 13th this year, so let's kick off the weekend a little early with another great round of reader questions.
✈️ I'm leaving on a jet plane
train_wreck asks:

Happy Friday (the 13!) Quick question, what airline do you usually fly to Mexico, and how is the experience WRT delays, service quality, etc. Are you able to get direct flights or do you connect?

Before the pandemic, I flew a lot for work and pleasure, and I developed a series of habits over that time to make that as painless as possible. Since then, things have changed, of course. I only fly several times a year now, and it's mostly back and forth to Mexico City, with one or two other work-related trips (usually Seattle, so far) and then one or two other longer flights (Berlin for IFA last year, for example, and Hawaii later this year for the Qualcomm Snapdragon Summit). And so some of my habits are a bit less well-honed than before. This is both good and bad.

Among my habits are flying direct as much as possible, flying as early in the day as possible, and always carrying on my luggage. Combined, these things are an attempt to thwart the issues that routinely come up every day for airlines, airports, and their customers, where any number of things can go wrong and then have an escalating impact on the rest of the day. This is what made my return from Seattle the week of Build so infuriating: That plane had sat at the gate for two hours, and it was only after everyone got onboard that the airline figured out there was something wrong with the entertainment system; the flight was delayed by 30 minutes, ensuring that I would miss my connection in Chicago. Instead of getting home around 5 pm–I had woken up at 4:00 am in Seattle–I got there after 11 pm. That whole trip was like a proof point for my habits.

So why did I even have a connecting flight? A couple of reasons. Microsoft had scheduled a late Sunday afternoon on campus that I wanted to attend (as it turns out, it was almost pointless), and my direct flight from Newark would have arrived too late. There's a local airport that's only 20 minutes from home, and if I flew out of there, with a connection, I wouldn't have to deal with the nearly 90-minute drive to Newark, which would either be a costly Uber or a very long drive for my wife (almost 3 hours roundtrip). Reasons. I don't know.

Anyway. For Mexico, we have consistently flown on United, which has two nonstop flights to/from Mexico City every day through Newark. We have status on United, part of that grandfathered in a year after the pandemic, and then maintained since we fly enough, usually to Mexico City. These are day flights, about 4 to 4.5 hours in the air, and with only one exception I can think of, we've been able to fly business class on every flight, which is another part of those habits to help things go smoothly. A lot of this is credit card points: We use a United card to pay for everything and it racks up. We can board...