Hi
@Disdood and
Apologies if you thought you had accidentally stumbled into a Kitchen Appliance forum but it is a friendly group here and the discussion can sometimes drift wherever life takes us.
Congratulations on your new addition to the family. We did WDW often in those early years, including one trip where our DD was 6mo and DS 3y. Everyone told us we were wasting money taking them to WDW as they wouldn't remember it, but I can tell you that the memories (and photos) from those trips are treasured by DW and I. Staying on Disney property is a real bonus with kids that age as it makes it easier to return to the hotel for a mid-day nap. WDW is sensory overload for young kids and planning some downtime to relax and recharge is so important. A one bed apartment is great if you can swing it, but if not a room with a balcony is helpful so you and DW can have somewhere to hang whilst kids are napping. I am not a DVC expert, but many here are and there are also DVC specific boards on the DIS which I am sure you have found.
As for credit cards, you mention that you have only 1 new card in the last 24 months. You do not state how many new cards your wife has, if any. One of the best ways to maximize earnings from new credits is for you (P1) and your wife (P2) to refer each other. For example, P1 applies for a CSP earns 60k Chase UR points. Then P1 refers P2 for a CSP which earns P1 10k points referral bonus and P2 gets the 60k for the new card. The level of referral bonus varies by card and changes from time to time.
There are so many paths you could take right now subject to your credit score and monthly spend. As you are currently 1/24 in terms of Chase, I would probably start there with either a CSP or CSR. The CSR annual fee scares many people but it comes with an easy to use $300 travel credit, better benefits and UR points are worth 50% more when used through the Chase travel portal. If you hold a CSP those same points are worth only 25% more. Points can also be transferred to hotel and airline programs. You would probably also look to add a Chase freedom card to take advantage of the 5% rotating categories. AFAIK, Disney hotels are no longer available on the Chase portal.
Depending on how often you anticipate flying in the future, you could look at the Southwest cards (also thru Chase) with a view to earning a companion pass that allows you to take a companion for free. However, as you state you haven't flown in quite some time, I am not convinced this is the right path unless you anticipate a significant change.
If you prefer to stick with Amex, then I like the Gold offer you mentioned. Again the P1/P2 referral strategy can be used. Avoid having each other as authorized users on your accounts. This will hurt your 5/24 count for Chase. Just be aware that Amex cards have a 'one bonus per lifetime' rule - and whilst there are occasionally ways around this rule - Amex cards are typically more difficult to churn than Chase. Capital One VentureX is another card you might consider. I even like the Citi Strata Premier, but many folks seem to hate anything Citi.
Bottom line - it is difficult to get specific with recommendations as you have so many options. The key is to start opening cards as often as your ability to meet the spend for the sign up bonuses allows, but maintain a reasonable pace - one card every 90-120 days or so for both P1 and P2 might be reasonable if you can meet the spend requirements. Seek to maximize referral bonuses and do not try to earn bonuses beyond your ability to pay off your credit cards in full every month. It is not worth getting into debt pursuing bonuses.