Key hole CC Pro with a Freud 70104 bit.
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That Helm is Awesome, great wood also
Thank you… I adore working with olive wood. It is a combination of the heavy figuring, wood smell and the finish one can get. I would usually sand to a polish that is hand-finished with 10,000 grit sandpaper then coat the workpiece with a light coating of beeswax. The beeswax accentuates the patterns of the wood, plus it adds something to the fragrant smell of olive wood.
The very heavy figuring found in olive wood does not suit some highly detailed subjects, but it is always fun to try and make nice things. Olive wood is very easy to machine while being just hard enough to contain tearout. The cutter was set to 18,000RPM and 2,000mm/min, which translates to 78.7IPM of traversal speed.
The toolpath was Carveco’s excellent circular toolpath which always produces a great finish on 3D carves. I start in the center and work outwards. The tip of the cutter is never following a raster path. The cutter tip is always carving new material with a circular toolpath. The cutter dimensions were taken from the first one in this list.
Looking closely along the internal curves of the helm, there are the tell-tale signs of chatter. The next piece will be carved a little less speedily in IPM terms. The tool stickout will be reduced by 25% in an attempt to control the chatter. I may increase the cutter speed to 20,000RPM so that I can end up with a workpiece that requires very little finishing.
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Did you program a toolpath or just jog with the bit running like I do for that? 
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Haha CC Pro actually has a keyhole feature; you just make a circle and then the keyhole tool path function allows you to choose the length and angle.
I am not replying for @RoughDraft40 but when I make keyholes I use the keyhole toolpath. Usually making a keyhole in the back of something is one of the last things I do. So I dont want to get a fat finger and screw up all the work on the front side. Here is my keyhole custom tool. You would need to modify it for your particular keyhole tool but it is a starting point. It is in pdf format because the forum would not let me upload a .csv file.
Keyhole+Shapeoko 3+Hardwood.pdf (16.4 KB)
Well, when I inevitably buy the pro software that will the bottom of my “pros” list.
Haha I get that. The fact that it’s there and works very well is nice though.
Commissioned to cut a design into a wood keystone at a chapel. Removed the existing keystones (2) and was able to get the design cut perfectly. Used my 5 Pro with an IDC 30 deg engraving bit (excellent bit BTW). Installed it looked awesome, IMHO. 
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I made a sign for one of our neighbors using the new inlay features. The main body is hard maple and the aspen leaves are different wood species. Clockwise from top left, I used eibiara, padauk, walnut, olive wood, padauk again, eibiara, olive and walnut for the leaves. I then V cut in the leaf veins and filled with epoxy. The name is just V carved and then painted. The frame is Wenge and designed so that the side bars aren’t attached to the tops of the frame to prevent it warping if the maple absorbs moisture at some point and swells. All of it is finished with Epifanes UV protective varnish, as it will be displayed outside.
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All of it looks good but my favorite is that large leaf with the olive wood in the top right.
Very nice looking box. Looks like 45 degree miters for the box corners. Did you use any splines to reinforce the corners?
Looks good!
For next time (or a rework), add some dark glaze to the lettering (or otherwise darken it; maybe add laser accents?) and make the chain components out of brass (if not gold.)
The garden-variety zinc plated chain diminishes your excellent project; just a bit.
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Thank you for the feedback, I will def do that, the brass would add a nicer touch and will use that in the future. There’s definitely a few things that I would do different next time but as my second project, I pretty stoked oh how it cam out.
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Cut template for a mechanical iris. the full template is for the leaves, the interlocking puzzle piece ends are for the 1/4 sections of the rings. (Size 9 flip-flop for scale) 
65" diameter overall.
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I saw this pic and I said out loud to myself, “Wow! That’s beautiful!” Awesome work
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