I'm very new to using Homeport and also to using GPS (got a Garmin 441 and Homeport software two weeks ago). Neither the chartplotter or the software are as easy and intuitive as I was hoping but everything seems to be working well. I just have a lot to learn.
However, I have done some playing with the google earth selection on the View menu in Homeport. It is truly amazing. It is one of the most useful features of the software I have seen. I'm still puzzled at how it works (two applications running at once with some integration). Google Earth shows my routes but not my waypoints. Anyway, to me, this feature makes the $30 I spent for the software worth every penny. If you haven't tried it, you should.