Hi Johnny,
You mentioned about skipping the HC08 and going straight to a S08.
I would STRONGLY recommend this to anyone starting out, as long as you can afford an S08 demoboard, just forget that the HC08 ever existed. You will NEVER regret this move.
Get a demoboard with a built in BDM or use an OSBDM with it. Use the latest available Codewarrior.