Ben,
This may be a silly question, but what are you doing that you need looping? I used to be quite good with looping and macros, but never bother anymore. Two reasons, almost no program size limits for PC based CNC, and inexpensive PC cam programs that do a much faster and more reliable job than I can. I use CamBam for $149 on my Mach3 homebuilt CNC and on the Servo 5000 bed mill at work. Programs take only minutes to write and you can use scripts and plug-ins to automate things still further. 40 free sessions before you pay, an awesome user forum, how can you beat that?