Pockets and plugs, am I missing something?

Hello folks,
How’re you all going about inlay and plugs? I’m doing a 3d piece with plugs going into pockets to stand higher. When I design this, I’m shrinking the plugs using scale, from 1 to .99-.98. This doesn’t always work though, because sometimes that’ll make a part of the plug too tight around another section. I’d love some insight into this or any advice to change my methods.

I’m running a shapeoko 3 xxl, with a 102 bit into 1/2 and 1/4 mdf. Designing in Carbide Create.

Could you upload the files you have tried thus far and matching photos?

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