Agreed. What I do is use as many parametric modifiers as possible. Smooth, Shell... Max 2016 has QuadChamfer now. You can put a Smooth modifier below it, with the desired angle treshold, then in QuadChamfer you can just choose "chamfer all unsmoothed edges".
This is actually three settings:
1. All Edges
2. Chamfer only Unsmoothed
3. Min/Max angle checkboxes disabled.
As for booleans, no clean topology can come out of this business. Instead, make excellent operators, ProBoolean them however you like, and use NO mesh-dependent modifiers above Pro Boolean, such as Edit Poly, or UVW Unwrap. Instead, when you want to edit something, go down in ProBoolean's own stack; and if it's awkward to edit from the stack, pick an operand and extract it (as an instance). Isolate, edit, ProBoolean magically updated itself while you worked.
Only parametric stuff should then go above ProBoolean, such as Smooth, Material, Normal UVW Map, Bend, etc etc.
Just an observation. If you plan to put much turbosmooth on it, then it looks to me like you arent modelling for performance/gaming. In which case, why are you worried about the topology? Just worry about the shape - and how easily you can get there, optionally edit it. Thats why I proposed this ProBoolean approach.