The first thing to do is to let us know where you are - city/county/state will be fine. It's important so that you know where in our database to find data, and other scannists in your area can help you along. Local help is sometimes best.
No, I think there's no software for the Mac - however your best choice would be ARC8 from BuTel. You can get that through Scanner Master. Get a
premium membership and you'll have the ability to import data directly from our database into the software editor. Note that anything in blue is a link.
Most modern PCs don't have serial ports, so you will need a USB-serial converter. It's quite likely an off the shelf model will work just fine. There are several listed here (I'm unsure if the RS one would work - perhaps other BCT8 users would comment) along with tips about using Device Manager to help locate and debug issues;
Connecting scanners via USB - The RadioReference Wiki
This article will get you thinking about Trunking, a method of distributing many users on a single radio system...
Trunking Basics - The RadioReference Wiki
and finally, like any hobby, we have a plethoria of terminology that can be described in a glossary
Category:RR Glossary - The RadioReference Wiki
That should keep you busy awhile...best regards...Mike