I'm basing my recommendation on materials published by two different vendors of epoxy resins. While I think they are reputable sources for this information, I couldn't help wondering about a possible reason for this counter-intuitive approach.
Best I can figure out is that you avoid "stair steps" inside the repair if you go largest first. These little steps create places where there's a bit of unreinforced resin, which weakens the laminate. On the other hand, going largest first, all the "steps" are at the surface where you'll sand them smooth, and as long as the repair is shallow enough to allow the laminate to conform, there's no space that isn't filled completely with glass.
Also, if you go smallest first, you have to be perfect in sizing your patches, while in the largest first method, any excess is sanded off at the end, so you only need to make sure you do have a bit of excess, but don't care whether it's exact.

- Different ways of stacking laminate to fill a shallow repair
- Laminating-A-Patch.gif (24.21 KiB) Viewed 3477 times
What I can't answer is whether the difference reflects a level of theoretical perfection that isn't noticeable in practice, or whether it matters. I suspect the answer to that will depend on whether the laminate being repaired is overdimensioned for the loads it experiences. The closer it is to minimal required strength, the less infidelity in repair you would be able to tolerate. Some part of the DS hull are truly overbuilt, but the flat sections of the rear hull may experience forces that are closer to the design limit.
I have nothing riding on how either of you does this, but I felt like sharing my personal level of understanding on this issue. So, now you have all the info to make your own decision.