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Worried about Cash On Arrival Schemes for Italian Apartments

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We are considering several rentals in Italy, some (mostly the US-based agencies) require prepayment and others (Italian owners and agencies) want much of the payment cash on arrival. I would appreciate hearing what others think about this practice that makes me nervous.

My wife says I am over-thinking it, but that is what I do best, and here are my concerns. I would appreciate responses.

1. Obtaining a couple thousand Euros in advance from the US is difficult; I have to order from my local bank a week in advance and maybe worse, their exchange rate is poor.
2. If I were to try to withdraw the funds from an ATM in Italy, I think I’m limited to about €300/day not enough to pay for my rental on my day of arrival.
3. Traveling around with a lot of cash makes me a nice target for a thief.
4. I show up at an address in Italy in a totally jet-lagged state and hand over a big wad of cash to a total stranger who claims to be the person who should receive it, but how do I know? Maybe s/he just waylaid the real person, took the key and then my money.
5. What if the apartment is not the one I thought I was renting? (I see many references to this shady practice in these forums.) The stranger can shrug and say, “Ciao, then don’t take possession.” I can walk away, of course, but someone has my deposit money and I have no place to sleep.
6. Or what if the apartment is deficient in some serious ways? (Again, I see many such cases in these forums.) The stranger has all my cash. There is no way I’m going to get that back. I have no leverage as I would with a credit card payment.
7. What if there is a break-in or serious problem and I want to call in the Police? The stranger with my cash could deny anything, even that we are tenants.
8. What if the property is somehow an illegal rental? I can think of many scenarios: the owner is out of town and doesn’t know it is being rented for cash and comes home unexpectedly. I read about that happening.
9. Or what if it hasn’t been registered with the local authorities? It seems like there are some registration requirements so the city can collect a tax. If I go to the authorities for any reason, maybe I have an illegal rental and what will they say or do? I can imagine everything from a shrug to being put in jail.
10. And finally, we all know this cash on arrival scheme is a tax dodge. I pay my taxes, I complain, but I pay because that is how my community and my country manage to provide me with a pretty good and safe place to live. If I am supporting the Italians' tax avoidance, then I am supporting their underhanded and illegal actions to avoid taxes which is causing their whole country to be on the verge of economic collapse.

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