i really like the two toned look here it sets the quilting off in an eye appealing way
some people use those diamond shaped cutters
in which case to start you would have for ex, an 8" cake on an 8" board
so you can get the cutter up to it without being prevented by hitting the larger board
then place it on the larger board after marking it
or some people use a ruler
fondant or buttercream either one--they are just different not one easier i don't think
fondant you wanna get it impressed right after covering of course so it will still be accepting of the marks--you don't want it to 'crust' up on you
oh and just kinda measure it out all the way around first without touching it so you see how much 'play' you have where the end one meets up with the beginning one--plan out the seam in the back so you know where you can can tweak in advance