Hmmmm.
Interesting concept- I LIKE IT!
A coupla things to mention though....
2 stage cooling (pool water to pc water) adds another layer of heat transfer and inefficiency to the system.
Unless your computers are all on the pool deck, you will need a pretty strong pump to keep the pc water flowing as you want.
A standard pc-type radiator is probably not what you would want in such a system: something that allows freer flow around it and much higher volume INSIDE it seems to me to be a safer bet. I am not a thermal/liquid dynamics guru though, so I would suggest a boatload of research on THAT point before spending crates of dough!
As far as whether or not the project is worthwhile in a pure "bang for the bang" sense- I am quite sure it will not be: a good pump will be expensive and so will pipe/tubing to connect everything. I am pretty sure you could get cooling results just as good (or better) for far less money.
I know that my Project Overkill would cost an insane amount if I had to pay for all the parts I am using. And I wouldn't be doing it. (I am C H E A P.)
But as for will it work? Yes, I think so, and it sounds like a very interesting project as well. It probably will make little difference in the pool temp, but with a large enough (surface area and flow) heat exchanger (radiator) it should definitely cool a bunch of computers.