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I don't know, guys, why are you having problems with these progs.
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Well, the only real reason why we do not recommend DOSBox to him is really because of his computer speed. He will never be able to emulate a 'new old game' with it because he won't be able to play with the cycles to bring it to the right speed. DOSBox require something like 1000mhz to run efficiently and at the correct speed for some game. It is extremely power hungry, especially if you consider it's made to emulate a 486/pentium at best!
For VDMSound, I have XP and I use it all the time. It would only not be usefull for Win98 since he already have DOS sound compatibility with Win98. All he have to do is write a Autoexec.bat and a Config.sys with a line for his soundblaster (or audio drivers), one for EMS and XMS and then the rest (i.e. anything that your DOS games will need, like a mouse driver for example) and it will work fine.
I used Win98 SE for 5 years and
never had a problem with it, apart from the occasional crashes which were extremely rare unless you were trying a new piece of software. Agreed, you had to reboot every 5 hours or so to continue using maximum efficiency... But then what's wrong with that? Just part of the game.