I haven't heard of anyone yet that didn't get the bit smart strips to work eventually with bit smarts help.
I've bought 4 of the sears current sensing ($20) power strips and have never had a single issue with making them work.
It sounds to me like what your proposing would require hacking the tv switch. I haven't heard of anyone with a tv that didn't power up after being unplugged that couldn't resolve that by jamming something like a paper clip into the side of the power button to hold the button down so that it would come on when you plugged it in. Most people are going to be hesitant to opening up there tv, especially if all you have to do is jam the button and effectively get the same thing.
It makes the most sense to use the PC to control everything else because it needs to be shut down properly. I don't know about 98 but with Win2k and XP pressing the power button initiates a orderly shutdown and closes your applications then shuts down windows then turns off the power to the pc. This makes it front end independant and requires nothing additional. If you can reach your pc through the coin door you don't even need to hack your pc to get a remote button for it.
The current sensing power strips can be used by almost everybody. The bit smart one is even a surge suppressor and is safe for sensitive electronic equipment.
I'm not trying to rain on your idea because it may fill a niche I just think you might be surprised by how small that niche is. For a while there where relay hacks for sale on ebay but I haven't even seen one of those for a while. I don't think there was enough interest in it and it still required opening your PC to get power to trigger it. I think Bit Smarts strip is competively priced for what it does and its tough to build your own for less than the Sears strip.
The reason one button power up and down is important to me is I'm not the only one playing my cabs. I have one in my in-laws basement that gets played constantly and having the one button solution is a requirement to get them to be able to turn it on and have them properly shut it down.
Don't let my negativity slow you down. I'm still interested in what your proposing especially how you would implement and control the time delay. A few months ago who would have thought we would have switchable 4/8 joysticks from above the panel that were as good as dedicated 4 and 8 ways?
http://groovygamegear.com/page12.html