You should be able to get the CPU up to 166MHz FSB at 1.75-1.80v without a problem. As to whether or not the rest of your system is stable, flip a coin and try it.
For cooling I suggest the Globalwin FOP32. For my 700@933 I use the OEM Intel cooler for 933 cpu's (the larger of the two sizes), which is inexpensive, quiet, and adequate, although not quite as good as the FOP32 for cooling. I have used this one up to 1015, where the OEM cooler reached it's limit. At 1029 it overheats.
You will loose stability around 55C. The processor can withstand higher temperatures than that, but you won't see them long before your system locks. PIII's have built in thermal protection. For stability I suggest that you keep your CPU temp under 40C at idle and 50C max under a full load.
Suicide is painless...........