Hard to say. My early revision k6-2 300 could go as high as 350mhz with stability, 375mhz with slight instability. Some of the later revisions were sometimes(not too often though) able to reach 450ish mhz. Don't expect too much and you'll be happy.
Cooling is good!

I wouldn't spend much on cooling, simply because the true performance gained is hard to justify the cost of expensive cooling for. An Alpha PAL6030 would probably be more than enough.
BTW, you can acheive a mild FSB overclock with those SS7 mobos(110mhz..maybe 112). Due to the nature of the k6-2(offchip L2 cache), any fsb uppage helps a lot. Basically, 330mhz(110fsb x 3) would be at least as good as 350mhz(100fsb x 3.5). 350mhz(100fsb x 3.5) is better than 396mhz(66fsb x 6). You'll have to play around a bit to see what fsb/multi ratios are stable, then run some benchmarks to see which of the stable ones are faster.