I am not as familiar with using Photoshop for graphics only. My main application is for photo touchup and enhancement. I have made some really cool art starting with a photo as the basis. It wouldn’t be much different to start with a blank screen and create your own artwork with the pentool as shown in this youtube video http://www.youtube.com/watch?v=SoeI5QQ7_no. I have used the pentool quite a lot to enhance various photos. There is also some good stuff using the brush tool as shown here http://www.sitepoint.com/graphics-photoshop-brushes/ that can be used in website design.
Unfortunately, I have no hardware recommendations for your application. I have a 27” non-touch monitor and a workstation. My drawing and text writing experience has been with the clumsy coordination of a trackball mouse. I, too, will need a stylus and touchscreen if I do graphics in any quantity.
I have no experience with Creative Cloud. I use the stand alone CS2 that I purchased about 5 years ago.
It sounds like you and your stepson are both tech savvy, so you will not have any problem with CS2 once you reach cruising altitude. It does have a learning curve, but I doubt that you’ll find it frustrating because it is intuitive. You’ll master the easier parts quickly and build on them.
Photoshop is an industry standard and you will never outgrow it. If you branch into photography, also, the possibilities for enhancing and modifying photos are nearly endless. It could be another art avenue for your stepson to explore. The results are so professional that it will amaze you. All the forums I have been on, people use Photoshop and speak in terms of it.
If you decide to do digital photowork, I would recommend getting Scott Kelby’s book on CS2. His writing style is entertainingly witty and easy to understand and he covers a lot of professional techniques. I am sure that there are similar books pertaining to graphic art, but I have not searched for them.
Thanks!