I have no experience with milling, but I do have a drill press and I have read through several "how to" threads on milling and it doesn't look all that difficult. I initially thought I would do this too, but I have gotten busy enough with murdering chips with inlays that I am not looking for more to do.
With that said, I would think you should be able to figure out how to get good results without ruining more than 5-10 chips. Getting efficient AND good results will likely take several hundred or maybe even up to a few thousand chips
The trick to getting efficient is you have to experiment with different ways of saving time. For example: how to reduce the # of times you pick up the chips etc. Little small things can make a big difference