Land line / Internet
Ascoli Piceno has a well developed fiber-optic infrastructure, especially in the Centro. Most apartment buildings have pre-existing telephone cabling, and many such systems are already hooked into the Ascoli fiber. If this is the case for you, setting up service should be easy and only requires digital provisioning and a technician coming to your house with a modem to plug in to your telephone port. There are numerous hardwired broadband providers: TIM, Vodafone, and others. The cost should be at most 30-40 Euros per month (with rental modem), and given that the Centro is wired with fiber, bandwidth should be excellent (>100 Mbit/sec). If you live in the suburbs or countryside, your mileage may vary.
In most cases, landline telephone service is provided as part of an Internet package with a telephone plugged into your modem. You probably can buy just telephone service, but doing so is not so common these days.
Communicating with Others
WhatsApp is very commonly used in Italy, probably more so than email. WhatsApp uses cell phone numbers as identities, so having a viable cell phone number is essential. It does not have to be a local number. There are PC and iPad apps that provide a WhatsApp interface, but they require your phone to be nearby (unfortunately).
Various government functions use PEC (authenticated, privacy-enhanced email). Setting up a PEC account involves setting up an account with one of the several PEC-provider services. Basically they need to authenticate you, and they all do it somewhat differently. Unfortunately, PEC email is not compatible with ordinary email agents (e.g., GMail, AppleMail).
Another bit of security technology you might run into is SPID, which is an authenticated digital identity system. You can get credentials in this system, for example, to access mycupmarche.it, the online SSN appointment system in Le Marche. There are various SPID providers (for example infocert.it). Setting up an account again involves authenticating your identity rather carefully with the help of a third party.
You may want to arrange to use a VOIP telephone provider for international voice calls. Some VOIP providers, like Google Voice or Skype, allow you to make free calls to the US from your smart phone or computer. In some cases, there are fees involved (such as when calling a US phone number using Skype). In other cases, you need to have set up a digital phone number (for example a Google Voice number) ahead of time.
Cell Phone Service
Cell phones are almost always unlocked in Italy. When moving from the US, it is therefore important that you make sure your US phone has been unlocked by your US provider.
The most common means of obtaining cell voice/data service is to establish an account in which you arrange to deposit sufficient funds to renew your chosen services when they expire each month. You will thus have to “ricaricare” (recharge) your account periodically. These funds are also used to pay for services in excess of your contracted service. There are plenty of service providers to choose from (TIM, WIND, Vodafone, Tre, Iliad). Some providers offer attractive plans for coverage in other countries (e.g., the US) when you visit there. Others do not. You might want to check.
Cell phone providers often try to sell you additional services, some of which can be a bit dodgy. It is not so difficult to subscribe to such services by accident, thus accruing regular charges that are not readily visible. So, it’s best to check your account billing details from time to time. It may also be possible to instruct your provider not to add additional services.