I think my fuzzy Disney math is winning out... I know we have our two trips this September, obviously. And then we plan to take the ILs on that cruise trip next June, which will include one or two park days. So I ran 3 scenarios for June... tickets plus dining for one day, two days with cheaper dining, and two days for more expensive dining. Compared dining discounts for Disney Visa, APs, and TIW.
Lowest cost scenario, we would be paying $240 more than we'd need to both get APs vs getting one AP for discounts, and TIW would cost an extra $12 even after discounts vs other discounts.
Medium cost scenario, we would be paying $140 more than we'd need to both get APs vs getting one AP for discounts, but TIW would save us $21 more vs other discounts even after paying the $150.
Highest cost scenario, we would be paying $70 more than we'd need to both get APs vs getting one AP for discounts, but TIW would save us $42 more vs other discounts even after paying the $150.
If DH and I sneak in just one more trip over the year, say a weekend trip with 2 parkhopping days... we win in all scenarios. See fuzzy Disney math...
ETA: And what if we did something really crazy, like went down in August next summer and celebrated our anniversary early before the APs expired... Or what if I can get a refund in the difference for DAH for APs, which is around $60...
ETA2: And this does not account for any souvenir discounts... before those in low cost scenario, we would need to spend $190 over the three trips to break even. DH will not have a problem with that

Other scenarios are already lower before any souvenirs.