What are you using to generate the G-code for the machine to run? Things like lead-ins, kerf offsets, pierce moves, etc are best done in a good CAM application. SheetCAM has automatic lead-ins and all the other parameters above and you can control start points by clicking the "S" cursor tool and moving the start point visually on the toolpath. If you are running the WINCNC version of Practical's machine (and probably BOBCAD?) then there is a POST in SheetCAM for WINCNC.
If you don't use SheetCAM then you will have to make a lead-in on your drawing and make sure it is the first node in the chain. I don't know if there is a way to re-order the nodes in BOBCAD.