Unless there is some specific exclusionary situation that causes you to not be able to obtain passports(I'm not asking you to explain it if so), you should do that(but I think it's correct that non-compliant states may be able to still use their DLs, assuming they have an extension granted by TSA). Unless you are also driving to keep costs down. You emphasized the TSA aspect, but then joked about still being able to feed your kids, so it sounds like you are also keeping good track of finances. You will waste so many days driving from the total opposite corner of the country, I'd consider that a huge negative. Yes flying probably costs more, but driving (gas, wear and tear on the car) and hotel stays along the way are not free either.
While it's true the DHS page for Oregon only lists 10/1/2019 at the moment, I believe they only update the extension date once the previous one has passed. You need to check with your state somehow (state web page, local representative, etc) to see if it is in the works for OR to continue to receive extensions. PA is in a similar boat, though at the beginning of the program PA was a bit belligerent with TSA/DHS, stating they would NOT comply, as the federally required cost was not something they felt PA should burden. So now that they are doing it, they just passed the cost to the individuals when they apply for the Real ID. You need to find out your state's situation. If they are making progress, they likely will be extended again.
Where are you staying? That makes a difference for FP+. You need to be on-site (normal on-site WDW hotels) or at one of the Disney "partner" sites (I forget the official name, but they are on the WDW site as well) to be able to get 60 days in advance FP+ reservations. Many of these "partner" sites are right near Disney Springs. You can only do 30 days without staying at one of these properties, and you can guess the top rides are much harder to get in that scenario. Cost-wise the WDW "value" resorts are the most affordable, and they get you the same FP+ access as the more expensive ones (Deluxes, like Polynesian, Yacht Club, Contemporary just to name a few).
How many people going? This may impact your choices of rooms that make sense for your group (one large suite(some at Art of Animation) vs 2 small separate rooms (could be worked almost anywhere) if you are say a family of 5 is a comparison point to be aware of).
Universal - compare the costs for one day with the express pass vs. 2 days without. The Express pass is a great help if you want to try one day. If you are already familiar with the CA park and don't feel a great need to just "relax and take it in" at all, then you can probably rush from attraction to attraction in one day with the express pass. Also evaluate your hotel stays - I believe if you stay in a Universal resort, you may get the express included. The hotels are certainly more expensive than the Disney value resorts though (possibly more than moderates and some Deluxes as well, I haven't looked lately).
If you drive as planned, swapping hotels during the trip will be no issue. If you do end up flying though, you need to consider airport transportation to and from. If you stay just at Disney, they have a shuttle from/to MCO included in your room rate. You can't use that to get to Universal in the middle of the trip though, you will need a rental car or Uber/Lyft/Taxi, etc it to get between the 2.
If you want to experience some of the dining options (nice sit down restaurants, etc), you need to think of that soon. Harder restaurants can book up quickly, and it starts 180 days form your trip (so you will need to try to reserve in September this year for your trip - 5 months from now or so).
I'd agree on the adding extra days vs capping. The cost to add extra days per day is somewhat minimal vs the cost of a single day ticket once you get past probably around 5 or 6 days. Even for the Universal days, in case you don't "feel it" and want to be able to hit a WDW park after wards, the limited extra cost can be worth it.
You have a lot to think about, start now! Good Luck!
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