OK, let's look at this then. On one side there is a tech light, spy non-existent, all jet country with NO defenses at all.
On the other there is a landthin dictatorship with almost maxed tech, mid range numbers of offensive and defensive military, and a gargantuan spy advantage considering the first country could have zero of them for all the effectiveness the few he has could possibly have.

So, strike 1 two jet SS, huge chunk of land take with some buildings. Drop the unused land.
Strike 2 two jet XX, huge chunk of land with buildings. Drop the unused land
Nest turns
3-10 turns blow up airbases (Pulling his teeth)

Strike 3 again a 2 Jet SS for land and buildings, drop the unused land.
Strike 4 again a 2 Jet SS for land and buildings, drop the unused land.

Next turns
3-10 bow up airbases

Consolidate my position at this point. Review intel on the now much smaller opponent. Assess how easy it will be for him to run turns. Refresh intel, of course.

Now we wait for his response. :)

How much damage was actually done to the 1st country vs how much, or lack thereof was costed to country 2? I'm certainly not looking for real numbers here, just the straight ratios would work for me. Or you can come up with some numbers and feel free to post them to support your argument that it wouldn't be profitable to do something like this. Outside the expected retaliation from his clan mates, etc. I already get that part.