If you have any aspirations to travel, you should virtually never cash in your Chase Ultimate Rewards points for cash. Why? You can transfer them to the Chase Sapphire Preferred, and then transfer the points 1:1 to airline partners, where you can approach 2 cents per point in value when redeeming for economy class tickets. Sometimes you can extract a ton more value, and sometimes less.
If you don't want to mess with airline points, you could also redeem them at 1.25 cents per point through the Chase travel portal (just book a ticket through it). But I don't know how close the fares are to fares you'd find on Expedia or directly with airlines.
I completely overlooked this. That's a very good point - in fact, we did travel to Asia and Europe in the past two years but I never thought about doing it that way. I just have the Chase Sapphire [non-preferred] card. I don't think I ever considered the Sapphire because of the annual fee. Of course, I have a Chase IHG rewards card, which has an annual fee of the same amount, and I do try to take advantage of that (however, I don't think I can transfer points between this card and the Ultimate Rewards points - or maybe you can but perhaps the exchange rate isn't as great).
I think I looked at the travel portal once and I feel like I recall not seeing much in terms of great deals. Maybe I wasn't looking in the right place or hard enough. The only thing I used the travel portal for, a long time ago, was for a car rental (I got a pretty good rate through that but never again after)
True, it has an annual fee. But it's waived in the first year. So a good strategy for the CSP, assuming it will still continue to exist and allow transfers from the Freedom and "unPreferred" Sapphire, is to build a bunch of points on them, and then apply for the CSP. Then cancel before the year ends (or downgrade to unPreferred, I guess).
Also, you say we, so I assume you have a SO. Your SO could also do the same with the CSP after you cancel. And I believe Chase points can be transferred between spouses.
And then, after your SO cancels, you can churn the CSP again - Chase is now explicit that you can get the signup bonus again if you haven't received it in the last 24 months. It says received, though, not opened card, so there may be a few months where you wouldn't qualify to sign up for the card for the sake of the bonus.