Welcome aboard, Gassman!
These are common enough questions, but sadly I can't count myself as an expert, so any advice I give will have to be considered in that light!
For the hobbyist, there appear to be two main brands of cutting machines: Silhouette and Cricut. Of the two, I'm really only familiar with the former, having purchased a Silhouette Portrait about 3 years ago (I think it may actually be a Portrait 2, but I'm not certain about that). I can certainly recommend that model as a good all-round machine, though I haven't used it extensively. It's main advantages for me were its relatively modest price, and its relatively small footprint.
In terms of software, I've found that the free edition of Silhouette Studio that comes bundled with the devices has covered everything I've needed to do so far. There are paid upgrades available for that software that unlock more features, but I haven't needed to take that step so far. It runs on both MacOS and Windows, and is upgraded fairly regularly.
I'll leave it to a member who uses a Cricut machine to describe their experiences with it!
Kev