SoulAssassin
I think your missing the point of overclocking for most people ,it's
free speed

,or maybe just a bit extra for a larger HSF.
All my case fans cost me nothing,all 2 of them

(X- AT PSU fans),even if they did ,they stay with the case whatever setup is/has been there.So its a 1 off cost.
I did buy a large copper HSF but only cos my old Ali HSF was barely up to the job & I needed another 1 anyway ,it cost me about £30 (about $45) nowhere near $100

.And thats the most I've ever spent on a HSF!
(I'd agree about the cost of water cooling kits but like you said for those people its the 'challenge ' factor

)
Also I leave my main rig running 24/7 & want that to be stable too ,true when
intially finding the CPU's/RAM limits there are stabilty problems ,but it doesnt take long to find the stable limit

,the only thing that costs is some time.
As for the benefit its much more than a few % for most of my rigs (present & past)
XP1600(1.4GHz)@1.6GHz ,that knocked about 40mins off WU times(down to 3.3hrs) ,about 14% increase in CPU speed but also FSB is up from 133 to 152.Btw I know this cpu will do 1.75Ghz(25% boost) to drop WU times down to 3.1 hrs,if I can get the damn L1 bridges connected properly! ,& yeah that is a lot of hassle but it costs very little)
XP1500(1.33GHz)@1.52GHz ,used the old Ali HSF from above rig
Cel 366@550 ,a nice 50% boost in cpu speed & FSB ,has been like that for 3.5yrs now with no probs

,just needed a larger than std HSF (about £5 at the time).This was definitely the best 1 ,very low cost & very easy

My PIII rig is probably the smallest overclock I've managed recently ,PIII 933@1035 ,about a 11% boost ,I needed a new HSF anyway & that cost me about £4
For me overclocking is the maxiumium gain with minimium (if any)cost
Like my mates rig ,1.2GHz Athlon ,overclocks to 1.4Ghz ,zero cost.