I built
Query The Net and have been at it for about a year. It's a meta-search engine that brings a bunch of shit together (wiki, Y!, msn, digg, google, blogs, etc). It's ugly & a bit slow (~5 sec.), yes I know ... but it works. Check out the
iron man page complete with trailer or find out where the
gay webmaster forum is on the internet.
As far as monetization goes, he really needs to figure out a way to set up
archives. Also, do some schnazzy .htaccess rewrite so his pages are friendly like searchquilt.com/search/keyword+phrase/ instead of q=keyword+phrase ... it makes it look a little better and is great for easily dropping links like so ( hxxp://querythe.net/best-results/gay:webmaster:forum/ ~~~ wf is #7 off the strength of Yahoo but it's not found in MSN or Ask because I use the intitle: modifier for "best results").
His 1st problem with getting archived pages indexed will be linkbait, perhaps you can help him there. In order for a decent number of pages to be indexed he will have to build shittons of links (~700 now so doing ok). I've got a couple links and about 25k pages currently indexed. Roughly 2000 visitors daily.
I monetize several ways, adsense brings me the most but it's not great ... definitely paying the bills though. Biggest suggestion for advertising, watch your log files and check out what visitors are coming for.
FYI: He is never going to get popular enough to even break 1/10 of 1% of the search market that is required to make a buck or 2 in that arena. So just forget about that.
Feel free to PM with any questions or get him in touch with me if needed.
Also, constructive criticism is ok from you pricks ... tell me why it sucks so I can make it better.