What you want to do is a "visa run" (or several). Some places have very explicit rules about that (e.g. the 90/180 rules of the Schengen Area), others are a lot less explicit, but they usually don't like it very much, and immigration officers have a lot of discretionary power.
I haven't found the relevant official text, so I don't know if there is anything explicit, but I would expect them not to like it — they make it clear that if you want to stay longer, you need a visa. Of course, if you plan to spend all your time and money in high-end hotels, restaurants and shops they will probably oblige.
- If you stay 15 days in mainland China, a month in HK, and then 15 more days in mainland China, this is probably not a problem.
- If you stay 15 days in the PRC, a night in HK, and 15 more days in the PRC, I'd expect issues.
- It may work once, but I would be very surprised if it worked multiple times.
I found a french visa agency which tells us:
Si vous devez entrer plusieurs fois en Chine dans l'année ou durant votre séjour, le visa double ou multiples entrées est conseillé, même pour des séjours inférieurs à 15 jours, notamment si vous passez par Hong Kong.
Translation:
If you need to enter China several times during the year or during your stay, a double or multiple entry visa is recommended, even for stays of less than 15 days, particularly if you are passing through Hong Kong.
But the solution is simple: get a visa! It's a little bit annoying, but contrary to visa applications for people from "poor" countries trying to enter "rich" countries for whom it can be quite difficult and the rejection rate can be high, the visa for an Italian wanting to visit China is really just a (costly) formality.
For visa applications, you are expected to show bookings for at least the first 7 days. I don't see any clarification about what information is required in the case of visa-free entry.