I am not a GIS guy by any means, just a techie that likes geography, mapping, and the outdoors. I've been making my own maps for quite some time, both for print and for my Garmin GPS. I've been steadily climbing up the GIS software ladder. I love the ability to pull in the raw source data from various places (USGS, State DNR, Google, etc...) and then lay it out and present it exactly the way you plan to use it.
My most recent acquisition was Manifold, and it is SWEET. Another great "bargain" GIS software gem is Global Mapper (
http://www.globalmapper.com/). It is what I was using until I discovered Manifold, and it is slightly cheaper for the same functionality (Manifold requires their "Surface tools" add-on to get the same feature set as GM). Manifold is a bit more powerful, however, as well as more streamlined. Both softwares have a great feature set, are relatively easy to use, and work very well with GPS receivers. Both packages also have AMAZING developers that listen to customer feedback, and have extremely responsive support (see the GM Yahoo Group @
http://groups.yahoo.com/group/global_mapper).
If you don't mind paying a few bucks for your software, either of these two GIS packages will give you a world of possibilities for a fraction of the price of "enterprise" GIS software (Arc*), and are far easier to use.
FWIW, I too am a Mac-preferenced user. My main desktop PC as well as my notebook are Macs, but I have a Windows workstation just to run decent GIS software. There is nothing even remotely comparable for Macs. The open-source GIS packages (GRASS, etc...) use extremely dated methodologies and are nothing more than an exercise in frustration (I've tried). They will do nothing except make you hate GIS.