No, I want to create the plots ahead of time, nice and neat obviously. Then proceed to walk and check each plot location to see if it is viable. If so I would return with containers and then publish.
GSAK, a macro and Google Earth, but Google Earth isn't great in some places.
It seems more sensible to me to walk your course marking options then uploading and going from there, but I'm not you.
Problem with that is I have no way to know when I am in the field if the spot i want will work as far as producing the art that will look properly on the map. I have a area scouted that will have enough room for the 48 individual caches that will comprise the art. I need to plot ahead of time to ensure distance guidelines and of course to make the art look good, evenly spaced, etc.