The quoted statement brought up a few questions I feel need to be answered before making a proper recommendation.
Are you felling or mostly bucking? When you use a saw, are you having to walk 100-500 yards with it, ppe, 2-5 gallons of fuel/oil, gallon of water, etc or can you pretty much drive up to it?
Also, you said you want a saw that makes you giggle. Well, what makes you giggle??
Speed or Torque? Do you want a high revving light saber or would you rather dog in, lean on it and watch the chips grow?
My 394xp will never rev like my 562xp. But with a 28" b/c you can REALLY LEAN on it and she'll just keep chuggin away which sounds absolutely fantastic. However, I've had to pack it into the woods and lug it around 6-8 hours at a time, day in and day out in a felling situation and it's a heavy HEAVY SOB. Probably 2 pounds heavier than a 390 and maybe a pound heavier than the 660.
About chains... Imo, and to an extent... they get better with time. As if they break in.