If you already have the programming cable and are premium member of RR programming the 106 will not be hard at all and yes you will need a trial version of programming software compatible with the 106. I use Win 500 and love it.
Here you will find links to the Easier to Read manual and a programming shortcut. At the bottom, go to the software article, and there are links to all the software (including Win500) that works with these scanners. Both ARC500 and Win500 have an article that serves as a user guide, which you also might find helpful