For your first question, yes, each traveller needs a policy that complies with the regulations...
...proof of sufficient medical coverage will be necessary at the time of
the visa application. Medical insurance requirements for the Schengen
- Minimum coverage shall be EUR €30 000 (equivalent to $50,000 USD)
- Cover must be valid within the Schengen region and for the full duration of stay
- Cover any expenses which might arise in connection with repatriation for medical reasons, urgent medical attention and/or
emergency hospital treatment or death
You will not be able to successfully apply for a Schengen visa without proof.
For your implicit question about EUR 30,000, this is the policy coverage amount. To receive this coverage you would pay the premium amount. You didn't include the length of your stay in Italy, but premiums generally start at EUR 30 - EUR 45 for the minimum coverage and increase according to any additional options you select. You do not have to put up EUR 30,000.
The price floor for these policies is set in the competitive market place, but it's reasonable to expect to pay a minimum of around EUR 30, even for a trip of 7 - 10 days. You need to enter personal details in order to receive a bookable quote, so a precise answer can be given only by a provider.
You acquire a policy (one for each person) using any of the myriads of providers and then print out the policies and enclose them with your Schengen application. To locate some providers you can search Google with the keywords: '
Schengen Health Insurance' (or a suitable translation of it).
Finally, the controlling reference for your question (i.e., the regulation itself) is at Travel Medical Insurance...