Good points Professor. What I've come down is some simple analysis between the two:
best comfort -> Image
best sound -> Custom 3
best price -> Custom 3
best availability -> Image (ha, for now at least)
What makes it difficult for me is that I still feel like Kipsch is marketing against itself. Instead of the clear decision found in the Custom lineup (how much are you willing to pay for better sound quality) you have competition between two separate factors (sound and comfort).
Even more difficult is the shades of gray that comes with this kind of subjective analysis. Will the Image be more comfortable? I would assume so, but significantly more than the Custom 3? Will the Custom 3 sound better? I would assume so but wouldn't the Image be good enough?
As long as the Custom 3 still show as "coming soon" the biggest factor is my itchy trigger finger because it's a one horse race. When they are both available I will have to weigh possible comfort vs sound quality.
Talking out loud a bit now ...
While it would be nice to have a pair of IEMs that is comfortable enough for hours of use, I wonder if that is what I really need. I'm not on long flights right now and my listening habits probably go in 1 hour bursts. So then my "requirements" are probably back to something that is comfortable enough for an hour or so. I would assume the Custom 3 would be "good enough" and have the added bonus of being the best available with respect to sound quality.
Then on the other side of the debate is the fact that many times in the past few weeks I've needed to concentrate at work and shut out the noises of the office. I still do sessions of an hour at a time but now I'm stringing several together. I end up switching headphones several times a day to try and keep the discomfort to a minimum. So in this situation I lean back to the Image and think the sound is probably "good enough".
Whew! Kind of funny how my mind works huh?

But I have to say there's been great support here. Kudos to you guys and gals for that. It's kept me away from looking at the Shure and Ety offerings for a few days at least.