Attached Link: Groboto

My understanding is that Poser doesn't like long thin polygons of the kind shown in your 1st screenshot - a model that contains these will have shading issues. So boolean operations that result in this kind of topology will be problematic but booleans that have a different topology will work fine.

I found a useful and cheap modeling app a while back called Groboto (see attached link) which is based on using primitives plus boolean operations. I've found the interface takes a bit of getting used to, but it's quite addictive, can make very complex shapes and can auto-generate quad meshes with pretty good (though not perfect) topology at varying resolutions. The helmet in the attached pic was 90% modeled in Groboto - some spheres and other default primitives plus several boolean operations. It also auto-generates UV maps based on the 'patches' formed by the primitives. Might be worth a look?

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