SC comes with some really good getting started documents and example files, and the web site has good info from SC and users.
Don't know which module or version you are using....(I use Advanced Milling V14.5)....however...here is a quick and dirty example....
1. Go into Planner and set-up your tools (EM, Drills, etc) and machine code generator.
2. Select the profile geomentry, copy it, and change the copy properites (you don't have to do that, that is the way I do it so I always have my original goemetric definition if I need it). You can select Tool, Offset, Z level, Clear, etc. You can then go set it up to start where you want and at lead-in lead-out.
3. For the holes, turn on a layer (say 250 for 1/4 holes) and put a point at each hole C/L (the snap function with place them there). Then select that layer and goto Process, Hole making. The menu will let you pick tools, depths and clear.
Like I said, quick and dirty example. SC has a lot of power and you can pretty well do whatever you want once you learn the system menus.