We have airline specific points for Southwest and American that we use. Those flights are easy to cancel up until the day of the flight if needed and the points are put back in our account. If we use the Chase points for air, you either need to purchase the equivalent of refundable tickets which is way more expensive and wastes points or there are other restrictions. Especially since Covid, I’m hesitant to book air through third parties (Chase uses expedia) because of the hassle getting customer service if needed. You also can’t transfer points from chase to American. (AMEX points can be transferred to Delta and used as Delta points!). I do look at fares occasionally, but they are generally higher on the chase portal than booking direct for some reason. Same issue with cruises through third party. We normally book refundable deposit these days and I cancel and book different cruises if I find better deals or we just decide to do something different. Love flexibility to change my mind.
As far as hotels go, Chase portal often has sales on varying hotels (dollar rates) that really make our points go a long way. Hotel prices are more dynamic than cruise or air fares and there are many hotels in the places we travel. This enables us to grab super great deals, especially if we book ahead. For example, we’re going to Italy in September and paying the equivalent of $200 per night in points for a $300 per night hotel room. Nothing against using for cruises or air, but it’s worth it to us to get airline specific cards (we also have hotel cards for the free annual nights!) for the free bags etc.