Whisker pole track on wood mast....

[Brion Toss]

Hello,
First, the side loads you speak of will be the same as you have now with those rings; where do you think the load goes to now? The difference will be that you will now have an athwartships stiffening member (the track) to help arrest those loads.
Next, the dotted line is not a good analogy here. True, if you just drilled the fastener holes and left the track off you would have weakened the mast, but you will be adding strength by adding the track. Think of it as being similar to gluing an extra layer of wood onto the face of the mast.
With the hardware loops on the side of the mast you do get the illusion of greater strength in that it looks like more of a compression load on a big surface. But in fact when the loads are highest you are likely to have huge torque and levering loads on the fittings, which is why you sometimes see them torn out. Now of course if you stuff the pole into a seaway things are probably going to give a little no matter what setup you have, but I think a properly-installed track will be stronger. And of course the track will give you far better, easier, more versatile sail control.
As for what constitutes a proper installation, be sure to epoxy-pot all those fasteners. Consider a long track, for on-mast stowage. Use well-spaced PX cleats for the 2:1 uphaul/downhaul. If you need explanations for these and other details, consider a consultation.
Fair leads,
Brion Toss