I can't tell you anything about using it with a Mac (since I don't have one), but you can download the free software (not the designer edition, but the basic edition) and see if you can get comfortable with it before buying anything. I do know that there are plenty of people who use the software on a Mac - and it didn't sound like they were using work arounds, but what do I know?
I can tell you that we bought my Cameo as a replacement for a "better" machine. The "better" machine was horrible to deal with and the software was, well, lets just say that it actually made me cry (and I am NOT prone to dramatics!) more than once. Silhouette software is actually EASY comparatively, and I was up & running as soon as the software was installed. The interface is very well designed and (mostly) does exactly what it says it does. Of course there are glitches, and updates can have issues, but I have yet to hear a bad thing about their CS either machine or software related. It's been just over a year now and I still ask my husband if I've mentioned how much I love it EVERY time I use it!
I don't have a dedicated space for it and it is kind of a pain to clear out space and set it up when I want to use it. However, it is worth every single moment of trouble! If money were no object I would absolutely go for the Cameo, mostly because you never know what you'll be wanting to do in the future. I would *never* have thought that I would be interested in vinyl - yet I spend a ton of time walking through stores exclaiming "I could vinyl that!" until my husband wants to gag me.
I say go for it! You'll love it!