In January, I booked a fairly complex itinerary for a trip to Istanbul and Malta in October. This was an award trip booked using United miles (all in business class, so...hard to get). Flights were a mix of United + Turkish + Swissair + Air Canada, so yes a lot of players and moving parts. Two legs outbound (to Istanbul), one leg in the middle (Istanbul to Malta), four legs coming home from Malta to Seattle (though, amazingly, that return trip was accomplished in one day -- a difficult thing to pull off coming from small market airports in southern Europe, going all the way to Seattle; due to flight schedules and major hubs, for us it's often a challenge to get all the way home in one day).
I got an incredible deal, which probably contributed to my lack of worry about how many dependencies it had.
A few days ago, I got notified by Air Canada about a "schedule change." Their new proposed routing would have us departing for our last leg home from Montreal before our trans-Atlantic Swissair flight arrived there, so we would need a time machine to make that connection. I looked at all the options to make it work. The best alternative would add more than 24 hours to our return flight, and work schedules make that problematic. So that entire itinerary collapsed, and I tossed it.
Yesterday I booked a different itinerary for that trip. It's a better, simpler routing, with fewer airlines, fewer flight legs, fewer connections. Also, the connections are significantly longer (and now are via cities that are less prone to long delays), so it should stand up better to minor schedule adjustments, and even a moderate airport "meltdown" as we've seen lately. I did pay more points for this more resilient (I hope) routing, but I have a lot more confidence it will actually get us there and home.
I booked this new itinerary about 24 hours ago. Ironically, within 10 minutes of completing the new booking, I got a text message from Turkish Airlines informing me that one leg of our original routing (which I had not yet cancelled) had a schedule change. Then, five minutes later, I got another text message from Turkish about a different schedule change which was for one of the legs on the new flight I had just booked no more than 15 minutes earlier! That's a record for me -- just 15 minutes between original booking and the (first?) schedule change. Fortunately the change was just a few minutes.
Several morals of the story here for me...
Expect schedule changes, maybe multiple changes. I've always looked at schedule changes as an opportunity to switch to a better itinerary (and I still do!) but sometimes the original itinerary is as good as it will ever get, and sometimes the only alternatives available after the schedule change are awful.
Resist the urge to stitch together clever, elaborate itineraries with many flight legs, especially if they depend on multiple connections & multiple airlines. Pay more attention to potential "failure points" and how badly your trip might be impacted if a single flight becomes unavailable.
In this era of "airport meltdowns" as we have seen at more than a few major transit hubs, allow way more time for connections than you might have wanted in an earlier era. I used to figure that a 90-minute connection in AMS or FRA was a little tight, but adequate. Not any more. My new flight connection in FRA is 5 hours and 20 minutes, which I am confident can withstand whatever chaos may be waiting for me there.
Likewise, when possible, make your connection in a smaller airport that is less prone to meltdowns and major delays. I switched from a 90 minute connection in SFO (they get fog and "ground stops" that can last hours) to DEN (this is not during snow season); I also switched one connection from FRA to MUC, which seems less prone to chaos.
It's an interesting time to fly. Stay flexible, be creative...and keep checking your flights!