<< Yeah overclocking a 286 wouldn't really help you gain performance >>
Actually, the opposite is true. Overclocking older chips (in the 486 and lower days) yielded performance increases closer to linear with the percentage that they were overclocked than they do now. This is simply because todays chips are running at very high multiples of the base clock, while older chips ran at the same speed as the bus (or at worst, no more than 3x the FSB). The cacheless chips gained even more from the overclock, as they relied on main memory for everything.