I choose that market due to affordability, potential cashflow and cash on cash return. 

The goal of the first 3 deals will be to target 1-4unit styled homes, requiring minor-rehab.

In 6 months they will be licking their wounds having given up on the system, now being that much further (by the amount spent, amount lost investing, wasted time, and emotional devastation) behind in realizing their goals and dreams 

The goal is to achieve and maintain financial freedom.

Currently I am looking to buy and hold for the long-term with the goal of being free and clear by the time I retire ~20 yrs. 

I see that I wasn't clear in my description of our current situation and our goals. 

You are choosing to lose money.

I choose Italy because I have a few advantages there.

Then you have someone who understands the investors goals well and the technical experts really working together effectively. 

Over the past eight years, I have collaborated with hundreds of out-of-state investors, helping them find cash-flowing properties aligned with their financial goals.