I have a few things I would consider in that situation
First, where you live. For example a place where it is HOT and sunny almost all of the year (say Florida where shorts and flip-flops are Christmas attire) you might gain something. In a cooler climate with a lower heating demand you might not gain as much. In a climate with a significant heating load, you may loose some heat in the fall shoulder season and into winter (at least until snow makes your room white for the winter . . . if you have snow that sticks), even with the lower sun and fewer hours of sun the, which would have to be made up by the heating system. Where I live I would would love free BTUs in the fall to spring and would gladly take the house warming a few extra degrees during the summer days.
Second, I would think that how you home is built would impact how much of a difference it makes. For example a home with an insulated roof deck and no ventilation would likely see a greater reduction when compared to a house with an attic that is unconditioned, well vented, and has the same amount of insulation on the floor.
Third, the condition of your roof. As you point out no one would likely volunteer to pay for a new roof, but you also shouldn't volunteer to put in money and time to paint a roof white that will need to be replaced soon (or before a reasonable payback period). But, it certainly should be a consideration in the next roof; just from my experience the attics under light colored metal roofs are cooler than the ones under dark asphalt roofs.
Fourth, cost of alternatives. I would compared the cost of doing a roof painting with upgrading the attic insulation (say to R-60) which would also keep the house cooler (and warmer too). True a white roof will still help at that point, but at a diminished amount.
It is an interesting idea that I have toyed with with in the past when I lived in warmer climates, but only as a thought experiment as I was renting at the time. If you move forward with it please let us know the results, I would be very interested to see how it works, but in terms of reduced cooling load and possibly increased heating load.