My guess would be that upping to I/O voltage will not be too fruitful. My understanding is that no one has ever been able to document the benefits of increasing the I/O voltage. It just "seems" like it could/should be helpful.
If your computer is freezing during the Win98 bootup then I would be looking at either the CPU or the memory as the problem. If you are sticking at or near the 100fsb mark, then it's not your PCI/AGP peripherals that are causing the trouble. Similarly, if your RAM is even decent, it should be able to handle any fsb at or near its rated speed.
Your chip is probably just not going to go any further...without more cooling. Try getting a larger HSF for your Duron. What are you using now? Anecdotal evidence suggests that the .18u Duron core will "take advantage" of extra voltage all the way up to 2.1v or 2.2v as long as there is sufficient cooling! Personally, even with a nice FOP38 or large Alpha, I wouldn't push the chip past 1.85v-1.90v if you want it to last for more than 6 months. As is, at 1.85 volts your Duron is probably just overheating.
Hope that helps,
Aaron