I used my CF Chiller with a siphon at first and found it near impossible...well let me rephrase, it took so long, I might as well have spooned out my wort, blew on it, then dumped it in my carboy.
I love gravity as a tool and refused to get a pump, so I dropped a whoppin' 25 bucks on a weldless fitting. Makes a HUGE difference, as I'm down to a reasonable 1.5 min per gallon rate. Now all that being said, its also fair to mention switching to a suspended hop bag couldn't have hurt either.
I would set my container of starsan on top of my basement steps with my SS kane attached to my CF, then I'd suck some starsan into the CF to get the whole thing filled up, once it started flowing out the other end I would pinch off the hose. Let sit for a few min to do it thing then I would transfer to the kettle. At that point I would release the pinch and let it run though until the starsan turned to wort, and I would start filling my carboys. All in all I prob had a 4-6 foot drop.
So to chime in with the other folks here, get a weldless fitting if you want to save your bud some frustration with his new chiller, in my opinion