Thanks to everybody who took the time to reply to my post and shared their knowledge on the topic.
Thanks to estiquaa for sharing the link to the Italian DMV with the official rules.
It turns out it is not possible to do what I had in mind, Art. 8 on the agreement says, how when you want to convert your current license with an Italian one, the Italian motorizzazione will verify how you obtained the license you currently have, and if they see you got it from another exchange and the original country where you actually took the test for it, does not have an agreement with Italy, then it wont be possible to convert it.
Crazy how different getting your license is around the world.
When I got it in USA I had just turned 18, took the practice test twice online, then went in paid $30 and passed the test, I barely knew any english... couple days later went in for the driving test, paid 50$ and passed that also, and that was my second time driving a car. Motorcycle license was even easier. And you can drive any car-bike right after you get your license.
In Italy however, for car and motorcycle license you pay about $1500, it takes 6 months and you actually have to study, then when you finally get the licenses you have to deal with a bunch of bs limitation, unless you are 24 years or older.
The best part is that when I went back to Italy for the summer at 18 years and the years after, I was able to drive-ride any kind of vehicle.... with my USA license...
Different tests for different driving styles and geological/weather factors.
The Italian theory test (if administered correctly) is actually one of the best Ive seen. They go into details around how a car works, suspension, brakes, etc. Not sure where in Italy you will do your tests, but, as everything in Italy, if you know the right people there are shortcuts for everything. I (oddly for once) don't suggest these, actually take this as a learning experience. Driving in Italy (with it's tiny streets, weird laws and driving culture) is much more challenging thand driving in the US (generalisation here... but my experience of American driving was in Nebraska in Uni, where the cars ablity to turn wasn't really seen as an important factor).
I hope this doesn't come across as condescending, but the limitations are actually quite good. I did a DAS in the UK the week I turned 24, and regretted it the week later when I bought my dream bike, and ended up on my side on a roandabout on my ride home (a Ducati 900ss ie for the record).
I then went and replaced it with a Cagiva 125cc while I got used to the roads, the wet, and the bike. By the time I saved up enough to repair the duke, I felt MUCH safer riding it.
Similarly, I did my first driving "test" (if you can call it that) in Africa at 14. The test comprised of "can you reach the pedals? can you drive in a square in a parking lot? Can you reverse? Congratulations!". I felt overconfident at the time, and looking back I had so much still to learn and was a danger on the streets.
A "few" years later (and MANY courses later, I've been fortunate enough to have the opportunity to continue learning how to drive through the MSA in the UK, with several "advanced motoring" organisations, a few police forces, and worst of all the UK's speed awareness course (in which the instructor drove MUCH faster than I ever would have on that road) and I realise that driving, like most parts of life, is an area where we constantly can learn.
In bocca al lupo!
M.