Hi,
I have a graphtec CE5000-60 which I think is ideal for starting up.
This also can be used to cut out printed vinyl such as transfers. You just print out registration marks and if will pick these up and cut round printed images etc.
I also use SignLab and CorelDraw as software. Both are good. Not sure but I think SignLab may be better, but CorelDraw is what I am familiar with for other reasons. The other option is Adobe Illustrator, which may be a good choice if you are familiar with it.
The Graphtec machine also comes with it's own software, but is a bit more basic, but should be fine for starting off.