That depends how you're going to provide connectivity to your Asterisk box.
If you plan to use your single analog phone line then you will be limited to its capabilities. For example, you can't do caller ID on the Asterisk box if your telco doesn't provide it.
If you're willing to get a SIP trunk (from a provider such as voip.ms or sipstation.com) you should be able to have all those features and many more. You'd want a reliable internet connection, and be aware of limitations such as E-911 service (or lack thereof.) Most distributions (Asterisk Now, PBX in a Flash, FreePBX distro) are simple CentOS installs from ISO and use the FreePBX web interface for configuration. It's all pretty straightforward.