Can I do the following?
Of course when I run, the data model will be incompatible since I have changed it without versioning. But since I will not be shipping the intermediate version, my suspicion is that the data migration should work fine when updating from v1.0 to the double-updated data model.
Is this accurate?
It will work as long as the following are true:
If all of that is true then it will work. And you can even go so far as to not ship v2 in the final build (although they are small and it is usually not worth the effort).
During development my recommendation is to always keep the v1 data around, only change v2 and remigrate every time you need to adjust v2. Then there is no intermediate to deal with. However that is not always possible when dealing/working with beta testers.