I am assuming here that the duscussion is about daily drivers, and one has to define the conditions of operation when one asks these types of questions.
Sure, thicker oil will give higher pressure, because the thicker oil is moving slower due to its higher viscosity. IF the oil flow is slowed or interrupted for some reason, then a higher viscosity oil may prolong catastrophic failure. Even with a high viscosity oil, I have yet to see anyone finish a race without some oil flow cooling the bearings and rings. In my view, thicker oils are only applicable for extreme situations and where fuel dilution from exotic fuels or rich mixtures would be a problem, or where you are running a totally air-cooled engine, and the major heat rejection (cooling) is via the oil.
You have to consider the application verses the viscosity. That's the tradeoff.
"At what point (regarding ambient temperature and engine load) becomes the advantage of a thinner oil and its ability to dissipate heat better - less important than protection from thermal breakdown?"
And again I ask the question, what do you mean by "thermal breakdown" of the oil? If you mean the thinning of the oil to a viscosity such that the hydrodynamic film is lost, then barrier additives kick in. The barrier additives will only prolong the catastrophic failure until the heat builds up and meltdown occurs. So my answer is that assuming your oil pump and coolant systems are functioning properly, the thinner oil (within reason) is the better choice for average driving, since the thinner oil will cool better, and you will not see viscosity thinning to the point of loss of hydrodynamic film.
If your daily driver sees oil temps averaging above 250 F, then you had better change your driving style or investigate why those temps are so high.
If this doesn't answer the question, then maybe an example of the conditions you speak of will clarify.