Order of Flooding and Outlining???

I am making snoopy cookies. My question is...is it best to flood an entire base covering the entire cookie and letting that dry then outline and fill the snoopy on top of the base coat OR is it best to outline and fill in the snoopy directly onto the cookie and then flood around it to fill in the surrounding areas???

 

I don't know which is best or if it even matters.

 

Help!

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