Now I'm a complete newbie at brewing, but for the last 2 of my 3 beers, I cooled the wort just enough so that I was comfortable with the idea of carrying it over to the fermenter, then dumped it in and diluted it to the full 5 gallons with store-bought bottled water. (I'd be more comfortable with the whole thing if I could do a full boil, but I don't currently have the pot to do it, and I'm not certain the electric stove could manage it.) Let it cool overnight to my pitching temperature of 64F, pitched the yeast in the morning.
I've had no problems -- the beer tastes good, oxidation and contamination haven't been issues, nor has DMS. Yes, there's some chill haze, but I consider that to be cosmetic and a side-effect of not yet owning a good chiller. However, if your sanitation isn't up to snuff, a long cooling period is risky.
ETA: I cover the hole where the airlock attaches with a piece of sanitized Al foil. You might be OK with an S-shaped airlock, but don't seal your hot wort with a 3-piece, as the liquid will be drawn into your fermenter as the headspace cools.