A much nicer cut on a Mets logo for one of my friends. Still dialing in my perceived depths (what I see on 3d preview vs what actually comes out on the wood) and playing with scrap wood. Sadly, the 88% of a coaster that was on the flip side was just deep enough to come through as a half circle on this one.
I think I may run the background pocket depth a shade deeper, and use a smaller bit. I have trouble seeing small details in the 3d preview, so I didn’t notice that there was an issue with some of the interior pockets that didn’t quite cut (the right ampit of the “Y”) right.
This is with reduced depth per pass down to .015 (from .028), 28imp, 3 flute straight bit a tad under 1/8"
Nice 
Is the depth you set not matching the depth actual cut? or is just not knowing what it will look like in real world?
Tip: make sure you set your material thickness in easel to match your work piece.
(the “Z” value on the materials tab)
That may help with properly visualizing depth of cut
You might want to do some calibration checking too. Make sure the right screw type for your z-axis is set up in easel as this will affect the steppes per inch value.
I don’t have anything to truly measure the actual cut…well, I guess I could just do a pocket that is out over the edge of the material just to confirm.
I have a really tiny 3d preview window. My mouse scroll doesn’t zoom (an issue with my machine) so I rarely get to see what a cut will look like on the preview.
So I have to go with depths and guesses. I do have to learn to double measure my material…as it’s never just the perfect 1/4" it says it is…
Though I sometimes feel the first pass is way deeper than the specified per-pass cut and subsequent cuts are normal…but I have not actually attempted to measure it. Maybe it’s my inexperience with machining and wood and hearing that grind and seeing the first cut. Maybe its a little bit of bowing in my wood. I still have leveling issues and until I get a 1/4 collet and bigger spoilboard cutter, I just don’t have the 10 hours it’s likely to take with my default 1/8 mills.
Try running some basic calibration cuts.
Load in some thicker stock, say 1" and do some 1/2" stair steps. If something is off it will be obvious.
At this point I would not worry about fine detail, Just that it is configured correctly.
As far as good “depths” for things, I tend to pick multiples of my bit diameter for my various layer “Heights” as this tends to match up with carving settings. The rest is style and experience as to what looks good 
Later you can see about tuning your setup for super accuracy
FYI you can get a pair of digital calipers for under $20
