Just to loop around on this in case it comes up in a google search later (and there's a lot of surplus information in here but it might help someone else out in future):
The source of my issue is/was that I use an unwrapper called RizomUV and it has the capability to overload an OBJ file with extra information that can be retained at the next opening of the OBJ file. Stuff which is only useful to RizomUV. So OBJ had been my go-to export for unwrapping, while FBX was my general purpose export for things like Substance.
The issue was that the latest version of Rizom correctly respects the normals in the OBJ file where before it was recalculating on import. That led me down the rabbit hole of trying to figure out how to get an OBJ with "proper" normals in it because the imported files became really hard to work with with blended/matched/averaged normals.
After a day of back-and-forth with the Rizom UV helpdesk it became obvious that they now also overload FBX files with that same information - great - I can use FBX now for pushing and pulling stuff in and out of this unwrap tool.
The last hurdle that made me think I still needed OBJ Was that every time I exported a model to FBX, it triangulated certain objects and surfaces, especially thinks like spheres, tubes, etc. (see attachment tube.jpg)
That totally broke the quad editing stuff in Max if I re-imported it. Can't do edge loop selection etc once everything is triangulated.
I checked my FBX export settings over and over and Triangulate was always disabled so I had no idea what was going on. Turns out - in the end - that I also had Preserve Edge Orientation checked and THAT was what was triangulating everything.
Once both Triangulate and Preserve Edge Orientation are turned off in FBX export options (see attachment export.jpg), I get "clean" FBX files that port much more nicely to both RizomUV and Substance Painter.