Since I cant account for what their money cost,I have found that is the biggest flaw.

I faced numerous hurdles and stressful moments, but I persevered and built a successful approach.To tackle this challenge, I recommend starting early by building relationships and seeking investors.

Fro the biggest reason, as you said, you own the home for the Best, First years of its life. 

The biggest issue is that forgetting to assign a location or choosing the wrong one can mess up your balance sheet, leading to inaccuracies.

My biggest desire is to have RALs.

And no matter what, keep an eye on how your financing structure lines up with your exit strategy.Where do you see the biggest risk.. sinking money into improvements or letting the buy back linger too long?

I’d love to hear from fellow self-managing landlords about the biggest lessons you’ve learned along the way—whether it’s handling difficult move outs, maintenance strategies, or unique ways to streamline day-to-day operations.

The biggest issue I see is that they are looking to restrict STRs in the area so why would I buy there knowing it could all go away.

There's money to be made whatever you decide to do but your biggest advantage is your age and time available to learn and grow.I have thought about house hacking for quite some time now.

While that is not a big hurdle, it should at least start to give you an understanding of the mentality the Italian government have towards business owners.