"My concern with going straight to the chest freezer was that I don't think it is good for it to run for so long. I am worried about it overheating."
The condensor is sized to reject the heat removed from the space when it is loaded with a certain weight of product. Product respiration and enthalpy are part of it. However, running a chest freezer at 50 or 60 deg. F. is harder on the compressor than running at 0 deg F.. NOOBs that toss in an electronic operator, set with a one or two degree dead band beat the compressor up pretty good. It's stop and go that rips up a compressor. The compressors are suction gas cooled and when the compressor doesn't run long enough, the suction superheat never gets to the point where the compressor motor is adequately cooled....I would worry more about the time it takes for the wort to hit pitching temps and using plastic buckets, than the freezer. Never believe that a 90 minute boil ends DMS and it won't come back. Chilling the wort isn't a waste of time. A waste of time, is waiting for the wort to cool. Chill the wort to pitching temps within 20 minutes and you'll make a much finer beer. Wort needs a quick cold break. Otherwise, oddball flavors come out and the "Ugly Baby Syndrome" that someone mentioned, comes into play.