Option #2 isn’t going to work. The whole point of testing on a VM is that you want to isolate your testing from the wreckage created by development. If you do your development on your VM, there’s no difference from doing it on the host Mac.
With regards your specific issue, in working with another developer I’ve discovered that VPN On Demand will only work on the Mac if your provider’s host app was installed by an installer. Thus, you have two options:
Option A is good for day-to-day development. Option B is a good test for how your app will behave on real user devices.
With regards option B, there’s no TestFlight on the Mac so you can’t use that approach. What you can do, however, is:
Run the app through App Review
Don’t release it to your users
Generate a promo code for the new version
Install the app using that promo code
Obviously there are multiple pain points here; feel free to file bug reports about the ones you find most painful. And, as always, please post your bug numbers, just for the record.
Share and Enjoy
—
Quinn “The Eskimo!”
Apple Developer Relations, Developer Technical Support, Core OS/Hardware
let myEmail = "eskimo" + "1" + "@apple.com"
WWDC runs Mon, 5 Jun through to Fri, 9 Jun. During that time all of DTS will be at the conference, helping folks out face-to-face. http://developer.apple.com/wwdc/