I'm also working on the programming of the skateboard trucks, which is proving to be much more complicated than I initially thought it would be.
My boss always emphasizes rigidity in parts making and should be one of the most important factors to keep in mind while programming. Initially, he instructed me to have enough material to surround the piece and create a wall around it; this would allow you to backfill it with clay or a casting material, reducing vibrations from the endmills. Unfortunately, I didn't realize that was what he meant until I had the stock cut and dovetails finished. So I had to take a different route and leave the lower half of the part completely connected to the base of the stock and fill it in with moldable clay rather than a liquid.
I'm taking advantage of the silhouette machining boundary in Fusion360 to create the base stock around the part, leaving plenty of material to hold on. Once I finish roughing out most of the material, I then come in with finishing toolpaths starting from the top and making my way down. Doing the top first will give me the most stability and so decreased vibrations. Once I finish up the upper half, I will then rough out the material connecting the part from the stock leaving a small amount at the bottom base and finishing the sides. It may not make the most sense and is hard to explain, but as I go through the process, it will become more apparent as I go through the project. I'm very thankful that this part doesn't have an NDA, and I am free to show the process that I am taking.
It's more complicated to do than on my Pocket NC, and I have to keep many more variables in mind while programming that wouldn't have been an issue on the smaller machine.