Wouldn't that involve having his not particularly tech savvy friends and family install a utility to generate the WoL packets and forcing them to do this unusual task when all they wanted to do was see some pictures in their web browser? I suppose if he had a fancy enough router, he could use that to trigger some sort of WoL event whenever port 80 was accessed and then forward the traffic to the awakened web server . . .
WoL packets can be generated by a bit of script that can be run from a web server. There are pages on the web where you can plug in the address, etc. to generate said packets.
So I would assume that one could put together a URL that would submit the right stuff to one of these servers.
(i.e. capture what your browser actually sends back when you fill in values and hit the wakeup button.)
Take that incantation and feed it into one of these sites that gives you a simple URL to access a complex one, and I would guess that one might be able to hide it all in a simple incantation. Might even get it down to one that does the WOL thing and then directs you to your web servers page.
(Disclaimer - I haven't done this, and as always, the Devil is in the details.)
I don't have the bookmark right in front of me for where I read about this,
but this might give some useful links on the topic.
http://lifehacker.com/348197/access-you ... ake+on+lan
And the wikipedia entry for Wake on Lan
has a bunch of references/howtos/web wakeup pages/etc.
As you say, configuring the router to send WOL packets is another route.
I asked about this here a while back, and got a couple of useful pointers.
http://www.silentpcreview.com/forums/vi ... highlight=
So setting it up might be a little technical, but should be possible to make it quite civilized for the user.