Hi and
to the travel hacking thread! I see you've already received the standard get your Chase 5/24 cards first. While none of the UR points will transfer to Alaska directly, there are Alaska Air partners that do get direct transfers from Chase UR points, like British Airways. So you can book Alaska Airlines using British Airways Avios miles, you just need to search for the availability on American Airlines website. If they have a saver award for an Alaska Air flight, then it is bookable with BA Avios. Sometimes, it will be less Chase UR points to book an award flight by transferring your UR points to BA miles than it will to pay for the same flight through the UR portal with your points. I will suggest to always check both options. Of course, you can also pay for your hotel stays with UR points. UR points in the CSR account are worth more than CSP and CIP.
We pay for all of our Disney vacations with Disney gift cards. Often times, we do get them at a discount. However, I find that purchasing them and getting 5x UR points either with the Freedom or Ink Cash/Plus is worth more than purchasing them with a 5% - 6% discount via Discover or Amex. If I buy $1,000 in Disney Gift Cards with the Amex for 6% cash back, I will save $60. If I buy $1,000 in Disney Gift Cards with a Freedom or Ink+/cash and earn 5 UR points which I would transfer to my CSR account I would earn 5,000 UR points which are worth $75 in the UR portal. Even with the CSP account they would be worth $62.50 which is better than the $60 savings. Once in a while we get really lucky and are able to combine the Chase UR 5x earning plus a discount. My personal combination to earn UR points is the Freedom and the Ink Plus which is no longer available but the Ink Cash still gets 5x at office supply stores which sell Disney gift cards. I also have the CSR and Freedom Unlimited. All UR points get transferred to my CSR account.
DH and I each have the Chase Marriott card since we get a free night on our card anniversary every year at a category 1-5 Marriott. We always use them at one of the 3 Marriott Village properties which are very close to WDW and also a WDW good neighbor hotel. One or two of them include breakfast with your stay. I find that the free night each year is worth the annual fee since I've never seen a Marriott for $85 or less.
Once you are past 5/24 or have the Chase cards you want/need I will suggest the SPG personal (while it lasts) and SPG business cards since SPG points transfer to Alaska 1:1. I will also suggest the Alaska card, both personal and business.
Other cards to consider down the line would be both Barclay American Airlines and Citi American Airlines. AA is an Alaska air partner and you can book AS flights using AA miles.
Hope this helps