I’m thinking of making a clock for a family member with a wood inlay. She’s a huge fan of silent movies, buster keaton in particular. couldn’t find a lot of art online but I did find this one that works well with image trace. I’ve never done a inlay before, think this design is a little too ambitious? Seems like some of the smaller details might not work out so well. Thoughts?
Depending what is the male or the female piece… I have watched many vids on this subject. The majority of people that do large in-lays cut the male into sections allowing them to place just that piece in, moving to the next. I would think that doing it this way would allow for minor discrepancies to be taken up by the placement.
What size? (workpiece & inlay), and what materials?
I might consider cheating the thinnest lines (right side of nose, top of hat, under right eye (our right, not his) a little bit bigger.
I just watched a cool video on infusing/impregnating wood with epoxy, which fills in the grain & would make it hold small details much better.
I would also start with a larger glue gap (bottom gap) than necessary on the male side, and then adjust accordingly.
That is a cool B&W image 
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You’ll be able to get mm level details in an inlay done with a Shapeoko. Materials matter, and I agree with @Tod1d that taking some time to hand edit the image will make it look better. That particular image looks to be of the type that has been lazily traced a few times.
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I was thinking roughly 12" round made from walnut and maple, hard to go wrong with that combo. I use CC and have been looking for a project to try the inlay mode. I recall seeing a few posts here a while back with folks getting mixed results with the CC inlay mode so ive just been a little hesitant to try it.