PYB is currently available through April 30 ‘21 on groceries, dining, and home improvement expenses. It hasn’t been announced whether it will continue beyond then, or for what type of purchases. I think cashing out your points is a personal decision. Would you rather have cash on hand now for future travel purchases, or do you like the idea of having a lot of points to book through their portal? For me the points have the same 1.5cpp value either way I look at it so I would rather have the cash now and set it aside for future vacations. Also by cashing out I’m not limited to using points on just the Chase portal. It’s really a matter of perspective. At the end of the day you’re still getting the same value for your points whether you cash them out or save them. I just “erased” $750 off my CSR this month. I will take that money I saved and put aside for future travel. Hope that helps
ETA: if your grocery store sells Disney gift cards, and you’re 100% sure you’re going to use them, you could buy them with your CSR earning 3x/points (until Apr 30) and use your points to erase the purchase. A great way to use URs to pay for Disney and potentially earn extra points in the process