Chase (and AmEx) travel sucks to deal with if you have an issue with your flight. Much better to book direct so you can deal with the airlines directly even at the cost of losing 3x. Same deal with points, much better spent by transferring out to an airline or their partner vs using them for 1cpp on one of the cards OTAs.
100% this. I book a decent amount of my leisure flights on Sapphire points only. Rebooking is trivial if you book directly with an airline, you can often do it within the app for that airline itself. Rebooking with Chase is often a 30-60 minute ordeal that can only be done over the phone involving 2-3 transfers. Often this is not even something that is your fault - the airline can rug pull the flight by changing the time or cancelling it, forcing you to undergo this ritual.
The funny (unfortunate) thing is that this used to be the opposite - years ago, Chase's in-house travel service was as close as you'd get to a white glove phone support experience in this day and age.
Then they outsourced it to Expedia, and the hold times went up and the efficiency and sanity of the whole process of dealing with any minor adjustment to your flight or travel plans degraded precipitously.
It seems like in 2021, they bought the company that was providing the backing technology for the in-house version of the service and have ditched Expedia again, so maybe this has gotten better since my last stint of big international travel?
If there is a security issue with the airline better that the intermediary has your payment information rather than the airline. When Cathay Pacific got hacked I was glad I had booked with (RIP) Vayama. Of course if this is an airline like Thai Airways that has you present the payment card at check in this might be pointless (and of course Apple Pay has obviated it too)
Can one transfer the points immediately before booking or is that process too slow. This way one could take adventange of fact that reward points do not expire.
Depends on the partner you are transferring to. Some are instant, like Delta, Southwest and United. Some can take a few business days like ANA. Always Google before transferring to determine actual average transfer time and never prospectively transfer points, always transfer with something in mind. Points could be devalued at any time without warning or expire.