FWIW, I just went through the same process the author of this thread indicates regarding the constant clearing of the filter as the wort is being funneled into the PF. It's a pain, even though I use a hop bag. I must have had to clean it 10 times yesterday. I don't see much of a way around this at this point other than to concoct a better filtration system as has been described above.
As far as the chilling goes, I still take the lazy approach and it seems to work fine. I use an immersion chiller and ice-bath to drop the temp to 80F in 10 minutes. Then I put the carboy in its fermentation spot - a wine cooler set for 65F - wait 4 hours, remove it, shake it, pitch the yeast, shake it and back into the cooler. As I said, works fine for me. I don't think there is any drawback in the 4 hours to get the wort from 80 to 65F - once it got to 80 so quickly.