There's so much good advice on this thread that my head is swimming and I can't decide what's next for us...so feel free to toss ideas my way!
Our goals: We're going to France in June 2018. Hotels, flights, rental car should all be covered by existing/planned points. Anticipate paying out of pocket for dining, sightseeing, misc - so, maybe a cash back card or something for that?? (Or maybe use Arrival+ or CSR to get points towards future travels). But I don't anticipate a whole lot more that we can do with points/rewards for France. Our next goal is to follow that trip up about 2 months later w/the 7-night Alaskan cruise on the Disney Wonder. We did book this at release-day pricing and use our onboard booking discount, so that helps. And we always buy discounted Disney gift cards to pay things to Disney, so there's at least 5% off. But, beyond that, I'm not sure how else to reduce costs. Maybe get some new cards and pay chunks of the cost on each to get rewards? (again, full payment not due until April and deposit paid already). We anticipate using free anniversary nights (probably Hilton, maybe Hyatt) for the Vancouver hotel. Though I could be swayed to pick up some other hotel card if there is a bonus that would be good for Vancouver (only hotel cards we have are Hilton Surpass and Chase Hyatt - we each have them). Third goal for 2018 is southern California for a cousin's wedding in October and hopefully returning to
Disneyland - however, we have virtually no dedicated funds left for travel just two months after the cruise and France before it. So, we'd really need to pull out every trick to make this work: free flights, free hotel, free rental car, and any Disneyland discounts possible (I know, not much exists). So, this is where I'm really thinking we need to pick up some new cards. For what it's worth, our preferred hotel would be the Best Western Park Place Inn, which we stayed at last time.
But, here's the catch. We are both now at 5/24. I get out of that this December, though, so thinking I should refrain from getting a new card until then (and get the CSP then to send my points to DH's CSR). DH won't get out until mid-2018, so I'm thinking we should just pile on the cards for him now. I don't want to waste time where we could be earning bonuses. We are currently finishing up spend on his Barclay Arrival + and just finished spend on his CSR (we can usually put about $2K of expenses on cards per month, total between the two of us). Oh, and both credit scores are still over 800.
So, what do we get now to make our goals happen? Here's what we have:
Chase Hyatt - both
Hilton Surpass - both (we also tend to stay in Hilton properties often when traveling in the US)
Barclay Arrival + - DH only (with plan for me to get early 2018, after CSP)
CSR - DH only (with plan for me to get CSP in Dec.)
Those are the recent ones, but we have some older ones we could still spend on, if it will benefit us:
US Bank Flexperks Visa - both (we had AmEx too for bonus, but just cancelled - that got us our France flights)
Delta Gold AmEx - both (haven't used for a while, but we are in a Delta hub - would have interest in getting Delta Platinum if good sign-up offer comes up again)
I have a super old Discover I used for the BJ's deal on Disney Gift Cards recently
Cash back card from my credit union (I think it pays 1.5% back on everything - I only used it for the intro bonus)
and various other old ones we don't use at all
What would be good to add and when (and who)?
Also, I've taken to opening checking accounts for cash too. I can't believe I've done this, but it's so easy! We both got $200 from US Bank (all online), we have a mailer from TCF for $250, so I'll have to go in branch or call to do that soon, and I decided to do the BMO Harris $200 offer too - just got DH signed up and will do mine after I do the TCF one (I think it's only 1 per household on TCF). US Bank allowed a $500 opening deposit via credit card (coded as purchase), so that helped move along some minimum spends. And BMO Harris allowed $1000 opening deposit with credit card...once that posts on DH's CSR, we're done with that spend - yay!

Once I open the BMO Harris, we should have another card we want to hit spend on for me to put that $1000 on (but need to figure out which one). Seems that I could also do $1000 for the TCF account, but need to do that soon and no current minimums spends to hit...hmmm.
Anyway, sorry for the rambling post as I think this through. Any suggestions on what to get next would be appreciated. Thanks!