We've done lots of split stays. What others have said is true.
A few ways we've made it work:
If you are going to end your vacation at a nicer resort, then maybe make that part shorter. Focus on hitting the parks hard the first part of your trip, and more time relaxing at the resort in the second half. AKL is a beautiful resort.
If free dining is part of your vacation plans, then maybe make the second part one night and skip the parks. When we've done our split stays this way - and we plan on spending lots of time at our resort- club level is a fun option. CLub level is relaly only worht doing if you will have enough time at your resort to take advantage of the club lounge, but it can be a fun splurge. The lounge at AKL is a very pretty vantage spot, and it will help offset your meals and adult beverage costs. (You get beer, wine, and cordials each day as part of the offerings)
Another option is to skip
DDP altogether. Consider getting an AP if the discount on the rooms is good, and pair it with Table in Wonderland. TiW gives you 20% off most table dining. You have to pay for it, but it gives you some freedom as well. It gives you 20% off adult beverages and appetizers! and you aren't forced to get dessert every night. You also get 20% off at AK park, and the value resorts' food courts. (Really I'm not much into drinking. But the cost of any drinks REALLY adds up quickly at WDW. Many are $10 a pop when you include tip.)
If you do DDP for the first part - your DDP credits don't expire until midnight of the day you check out of that resort - so you can maximize how you use your credits. Use cash to pay for the least expensive items or stretch your creidts by sharing. (At a QS place, get one entree and one 'snack' item like a cup of chili. Plenty of food for two adults.)
Disney doesn't truly do split stays maybe as we talk about onthe DIS, but they do recognize them. DIsney will allow you to keep using your tickets for 14 days, will transfer your luggage between resorts for free, and will provide ME from both resorts. So I think they do their fair part to facilitate such transfers. The only part that doesn't really trnasfer is some of the discounts and DDP. on transfer day - if you already have your tickets - you do NOT need to go to your second resort first thing in the morning. You can simply head to a park. If you have to go to the second resort to get your tickets, that is quite a bit more complicated and time consuming! You are MUCH better off if you don't have to do that because there is no direct transportation between resorts! You might as well get a rental car.
Incidentally, if you DO get an AP - DIsney now ALSO allows you to do DDP wihtout buy two sets of tickets.
So while none of this solves your dilemma, it does give you some pointers to consider; one of which may work for you.
Last, when we do split stays, I pack accordingly. How you pack makes a big difference in how easy it is to transfer. For example, if you put all the used laundry into one suitcase, then you don't need to open it at all in the second resort. Instead of packing suitcases for each person, pack in terms of first-half and second-half, and a joint bag of toiletries/bathing suits. At the end of your stay- you final packing is MUCH easier. (The trade off of having to pack mid-trip.)