Any way App Store (iPhone/Mac) can be LEGALLY set on two different countries?

I am Italian, I used to live in the US and I have a bank account both in Italy and the US, meaning I can easily switch App Store country just by updating my account info on the App Store. Having purchased my latest unlocked iPhone in the US, I've been set on the American store for almost two years now--it just offers more options--but my Italian apps (apps that are not available on the US store) won't update, and vice versa should I switch to Italy again. It's kind of a hassle because some apps just won't work if they're not updated, and I'm afraid there's a limit in the number of times I can switch country on the store.
Is there any way Apple helps bypass this "problem" by allowing users to set there account on multiple countries, or can I just make sure updates will download automatically even when I'm not set on the "right" country?
Hope my question is clear. I appreciate any useful pointers!
Enrica

i have two iphones one i use in uk and one i use in portugal
how about if i sync one with windoze for the portugal store and one with my mac for the uk store would that work?

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