With regard to checking whether you have met the MSR, I always go by payments made as it's easier to track than every individual purchase. That being said, with Chase's UR system it's easy. If you go into your online profile and click the "Redeem" button next to your UR total (even if its 0), it will take you to the Ultimate Rewards page, which will also show the number of points pending following your next statement close. If you have earned the bonus, it will be reflected in that total.
If you fly Southwest, this is the best time of the year to consider getting 2 cards to meet the Companion Pass requirements. Currently, all SW personal cards are on an elevated bonus of 75,000 miles. You can do the "modified double dip", which means getting approved for one SW card and then applying the next business day for a second one. Due to the narrow window, the system isn't triggered to prevent you from getting more than one personal card in the Southwest family of cards. You should hold off from meeting the MSR on those cards until after January 1, 2023, at which point you will have a Companion Pass throughout the remainder of 2023 and all of 2024. Alternatively, you could get a Southwest business credit card now and 1-2 personal cards in early 2023 to both receive a CP and stockpile a large amount of miles that you can subsequently redeem 2 for 1 due to the CP. Just make sure you don't come close to the MSR until 2023 as there are some data points that Southwest credit cards post the bonus miles early when you near the MSR.
Then my husband will quiz them "Who's too radical for Wisconsin?" 
