If you are looking at cycling your caffeine naivety with an eye for fitness benefit (caffeine increases exercise tolerance), I think you should first look into whether there is any true benefit to the cycling. You are talking about purposefully inducing a cycle of addiction/dependence and withdrawal, however, I am not sure I have ever heard that the exercise tolerance from caffeine decreases as caffeine tolerance increases.
In cycling (a sport I am familiar with) most pros maintain some level of caffeine tolerance. I've the routine before the day's workout is an espresso or two. I've never heard of cycling that caffeine intake. With a doping and performance maximization such a ever present in cycling, it seems like if there was really benefit to cycling, it would be happening.
This article suggests that the exercise tolerance is the same or similar regardless of the level of caffeine dependence. (actual study here) The most I could find online for cycling was some bodybuilding forums talking about cycling their pre-workout stimulants. Not really any specific information about what is contained in the mess of supplements they are taking.
Based on that study and the lack of information for cycling caffeine tolerance, I'd suggest that the withdrawal symptoms and side effects of caffeine consumption on naive individuals are not worth the purported but undocumented benefit of cycling your caffeine consumption. I think while it's true that some of the mental stimulation and other effects of caffeine may taper off with tolerance, the exercise tolerance benefit does not. However, individuals ignorant of this, or seeking mainly the mental stimulant part of caffeine effects, may resort to cycling their caffeine intake.
TL;DR The bottom line is for physical performance, there is not a reason to cycle. For mental performance there is a build up of tolerance and off periods would provide a benefit at the cost of symptoms encountered during the withdrawal period.